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Recent advances on the transition-metal-catalyzed synthesis of imidazopyridines: an updated coverage
- Gagandeep Kour Reen,
- Ashok Kumar and
- Pratibha Sharma
Beilstein J. Org. Chem. 2019, 15, 1612–1704, doi:10.3762/bjoc.15.165
Graphical Abstract
Figure 1: Various drugs having IP nucleus.
Figure 2: Participation percentage of various TMs for the syntheses of IPs.
Scheme 1: CuI–NaHSO4·SiO2-catalyzed synthesis of imidazo[1,2-a]pyridines.
Scheme 2: Experimental examination of reaction conditions.
Scheme 3: One-pot tandem reaction for the synthesis of 2-haloimidazopyridines.
Scheme 4: Mechanistic scheme for the synthesis of 2-haloimidazopyridine.
Scheme 5: Copper-MOF-catalyzed three-component reaction (3-CR) for imidazo[1,2-a]pyridines.
Scheme 6: Mechanism for copper-MOF-driven synthesis.
Scheme 7: Heterogeneous synthesis via titania-supported CuCl2.
Scheme 8: Mechanism involving oxidative C–H functionalization.
Scheme 9: Heterogeneous synthesis of IPs.
Scheme 10: One-pot regiospecific synthesis of imidazo[1,2-a]pyridines.
Scheme 11: Vinyl azide as an unprecedented substrate for imidazo[1,2-a]pyridines.
Scheme 12: Radical pathway.
Scheme 13: Cu(I)-catalyzed transannulation approach for imidazo[1,5-a]pyridines.
Scheme 14: Plausible radical pathway for the synthesis of imidazo[1,5-a]pyridines.
Scheme 15: A solvent-free domino reaction for imidazo[1,2-a]pyridines.
Scheme 16: Cu-NPs-mediated synthesis of imidazo[1,2-a]pyridines.
Scheme 17: CuI-catalyzed synthesis of isoxazolylimidazo[1,2-a]pyridines.
Scheme 18: Functionalization of 4-bromo derivative via Sonogashira coupling reaction.
Scheme 19: A plausible reaction pathway.
Scheme 20: Cu(I)-catalyzed intramolecular oxidative C–H amidation reaction.
Scheme 21: One-pot synthetic reaction for imidazo[1,2-a]pyridine.
Scheme 22: Plausible reaction mechanism.
Scheme 23: Cu(OAc)2-promoted synthesis of imidazo[1,2-a]pyridines.
Scheme 24: Mechanism for aminomethylation/cycloisomerization of propiolates with imines.
Scheme 25: Three-component synthesis of imidazo[1,2-a]pyridines.
Figure 3: Scope of pyridin-2(1H)-ones and acetophenones.
Scheme 26: CuO NPS-promoted A3 coupling reaction.
Scheme 27: Cu(II)-catalyzed C–N bond formation reaction.
Scheme 28: Mechanism involving Chan–Lam/Ullmann coupling.
Scheme 29: Synthesis of formyl-substituted imidazo[1,2-a]pyridines.
Scheme 30: A tandem sp3 C–H amination reaction.
Scheme 31: Probable mechanistic approach.
Scheme 32: Dual catalytic system for imidazo[1,2-a]pyridines.
Scheme 33: Tentative mechanism.
Scheme 34: CuO/CuAl2O4/ᴅ-glucose-promoted 3-CCR.
Scheme 35: A tandem CuOx/OMS-2-based synthetic strategy.
Figure 4: Biomimetic catalytic oxidation in the presence of electron-transfer mediators (ETMs).
Scheme 36: Control experiment.
Scheme 37: Copper-catalyzed C(sp3)–H aminatin reaction.
Scheme 38: Reaction of secondary amines.
Scheme 39: Probable mechanistic pathway.
Scheme 40: Coupling reaction of α-azidoketones.
Scheme 41: Probable pathway.
Scheme 42: Probable mechanism with free energy calculations.
Scheme 43: MCR for cyanated IP synthesis.
Scheme 44: Substrate scope for the reaction.
Scheme 45: Reaction mechanism.
Scheme 46: Probable mechanistic pathway for Cu/ZnAl2O4-catalyzed reaction.
Scheme 47: Copper-catalyzed double oxidative C–H amination reaction.
Scheme 48: Application towards different coupling reactions.
Scheme 49: Reaction mechanism.
Scheme 50: Condensation–cyclization approach for the synthesis of 1,3-diarylated imidazo[1,5-a]pyridines.
Scheme 51: Optimized reaction conditions.
Scheme 52: One-pot 2-CR.
Scheme 53: One-pot 3-CR without the isolation of chalcone.
Scheme 54: Copper–Pybox-catalyzed cyclization reaction.
Scheme 55: Mechanistic pathway catalyzed by Cu–Pybox complex.
Scheme 56: Cu(II)-promoted C(sp3)-H amination reaction.
Scheme 57: Wider substrate applicability for the reaction.
Scheme 58: Plausible reaction mechanism.
Scheme 59: CuI assisted C–N cross-coupling reaction.
Scheme 60: Probable reaction mechanism involving sp3 C–H amination.
Scheme 61: One-pot MCR-catalyzed by CoFe2O4/CNT-Cu.
Scheme 62: Mechanistic pathway.
Scheme 63: Synthetic scheme for 3-nitroimidazo[1,2-a]pyridines.
Scheme 64: Plausible mechanism for CuBr-catalyzed reaction.
Scheme 65: Regioselective synthesis of halo-substituted imidazo[1,2-a]pyridines.
Scheme 66: Synthesis of 2-phenylimidazo[1,2-a]pyridines.
Scheme 67: Synthesis of diarylated compounds.
Scheme 68: CuBr2-mediated one-pot two-component oxidative coupling reaction.
Scheme 69: Decarboxylative cyclization route to synthesize 1,3-diarylimidazo[1,5-a]pyridines.
Scheme 70: Mechanistic pathway.
Scheme 71: C–H functionalization reaction of enamines to produce diversified heterocycles.
Scheme 72: A plausible mechanism.
Scheme 73: CuI-promoted aerobic oxidative cyclization reaction of ketoxime acetates and pyridines.
Scheme 74: CuI-catalyzed pathway for the formation of imidazo[1,2-a]pyridine.
Scheme 75: Mechanistic pathway.
Scheme 76: Mechanistic rationale for the synthesis of products.
Scheme 77: Copper-catalyzed synthesis of vinyloxy-IP.
Scheme 78: Regioselective product formation with propiolates.
Scheme 79: Proposed mechanism for vinyloxy-IP formation.
Scheme 80: Regioselective synthesis of 3-hetero-substituted imidazo[1,2-a]pyridines with different reaction su...
Scheme 81: Mechanistic pathway.
Scheme 82: CuI-mediated synthesis of 3-formylimidazo[1,2-a]pyridines.
Scheme 83: Radical pathway for 3-formylated IP synthesis.
Scheme 84: Pd-catalyzed urea-cyclization reaction for IPs.
Scheme 85: Pd-catalyzed one-pot-tandem amination and intramolecular amidation reaction.
Figure 5: Scope of aniline nucleophiles.
Scheme 86: Pd–Cu-catalyzed Sonogashira coupling reaction.
Scheme 87: One-pot amide coupling reaction for the synthesis of imidazo[4,5-b]pyridines.
Scheme 88: Urea cyclization reaction for the synthesis of two series of pyridines.
Scheme 89: Amidation reaction for the synthesis of imidazo[4,5-b]pyridines.
Figure 6: Amide scope.
Scheme 90: Pd NPs-catalyzed 3-component reaction for the synthesis of 2,3-diarylated IPs.
Scheme 91: Plausible mechanistic pathway for Pd NPs-catalyzed MCR.
Scheme 92: Synthesis of chromenoannulated imidazo[1,2-a]pyridines.
Scheme 93: Mechanism for the synthesis of chromeno-annulated IPs.
Scheme 94: Zinc oxide NRs-catalyzed synthesis of imidazo[1,2-a]azines/diazines.
Scheme 95: Zinc oxide-catalyzed isocyanide based GBB reaction.
Scheme 96: Reaction pathway for ZnO-catalyzed GBB reaction.
Scheme 97: Mechanistic pathway.
Scheme 98: ZnO NRs-catalyzed MCR for the synthesis of imidazo[1,2-a]azines.
Scheme 99: Ugi type GBB three-component reaction.
Scheme 100: Magnetic NPs-catalyzed synthesis of imidazo[1,2-a]pyridines.
Scheme 101: Regioselective synthesis of 2-alkoxyimidazo[1,2-a]pyridines catalyzed by Fe-SBA-15.
Scheme 102: Plausible mechanistic pathway for the synthesis of 2-alkoxyimidazopyridine.
Scheme 103: Iron-catalyzed synthetic approach.
Scheme 104: Iron-catalyzed aminooxygenation reaction.
Scheme 105: Mechanistic pathway.
Scheme 106: Rh(III)-catalyzed double C–H activation of 2-substituted imidazoles and alkynes.
Scheme 107: Plausible reaction mechanism.
Scheme 108: Rh(III)-catalyzed non-aromatic C(sp2)–H bond activation–functionalization for the synthesis of imid...
Scheme 109: Reactivity and selectivity of different substrates.
Scheme 110: Rh-catalyzed direct C–H alkynylation by Li et al.
Scheme 111: Suggested radical mechanism.
Scheme 112: Scandium(III)triflate-catalyzed one-pot reaction and its mechanism for the synthesis of benzimidazo...
Scheme 113: RuCl3-assisted Ugi-type Groebke–Blackburn condensation reaction.
Scheme 114: C-3 aroylation via Ru-catalyzed two-component reaction.
Scheme 115: Regioselective synthetic mechanism.
Scheme 116: La(III)-catalyzed one-pot GBB reaction.
Scheme 117: Mechanistic approach for the synthesis of imidazo[1,2-a]pyridines.
Scheme 118: Synthesis of imidazo[1,2-a]pyridine using LaMnO3 NPs under neat conditions.
Scheme 119: Mechanistic approach.
Scheme 120: One-pot 3-CR for regioselective synthesis of 2-alkoxy-3-arylimidazo[1,2-a]pyridines.
Scheme 121: Formation of two possible products under optimization of the catalysts.
Scheme 122: Mechanistic strategy for NiFe2O4-catalyzed reaction.
Scheme 123: Two-component reaction for synthesizing imidazodipyridiniums.
Scheme 124: Mechanistic scheme for the synthesis of imidazodipyridiniums.
Scheme 125: CuI-catalyzed arylation of imidazo[1,2-a]pyridines.
Scheme 126: Mechanism for arylation reaction.
Scheme 127: Cupric acetate-catalyzed double carbonylation approach.
Scheme 128: Radical mechanism for double carbonylation of IP.
Scheme 129: C–S bond formation reaction catalyzed by cupric acetate.
Scheme 130: Cupric acetate-catalyzed C-3 formylation approach.
Scheme 131: Control experiments for signifying the role of DMSO and oxygen.
Scheme 132: Mechanism pathway.
Scheme 133: Copper bromide-catalyzed CDC reaction.
Scheme 134: Extension of the substrate scope.
Scheme 135: Plausible radical pathway.
Scheme 136: Transannulation reaction for the synthesis of imidazo[1,5-a]pyridines.
Scheme 137: Plausible reaction pathway for denitrogenative transannulation.
Scheme 138: Cupric acetate-catalyzed C-3 carbonylation reaction.
Scheme 139: Plausible mechanism for regioselective C-3 carbonylation.
Scheme 140: Alkynylation reaction at C-2 of 3H-imidazo[4,5-b]pyridines.
Scheme 141: Two-way mechanism for C-2 alkynylation of 3H-imidazo[4,5-b]pyridines.
Scheme 142: Palladium-catalyzed SCCR approach.
Scheme 143: Palladium-catalyzed Suzuki coupling reaction.
Scheme 144: Reaction mechanism.
Scheme 145: A phosphine free palladium-catalyzed synthesis of C-3 arylated imidazopyridines.
Scheme 146: Palladium-mediated Buchwald–Hartwig cross-coupling reaction.
Figure 7: Structure of the ligands optimized.
Scheme 147: Palladium acetate-catalyzed direct arylation of imidazo[1,2-a]pyridines.
Scheme 148: Palladium acetate-catalyzed mechanistic pathway.
Scheme 149: Palladium acetate-catalyzed regioselective arylation reported by Liu and Zhan.
Scheme 150: Mechanism for selective C-3 arylation of IP.
Scheme 151: Pd(II)-catalyzed alkenylation reaction with styrenes.
Scheme 152: Pd(II)-catalyzed alkenylation reaction with acrylates.
Scheme 153: A two way mechanism.
Scheme 154: Double C–H activation reaction catalyzed by Pd(OAc)2.
Scheme 155: Probable mechanism.
Scheme 156: Palladium-catalyzed decarboxylative coupling.
Scheme 157: Mechanistic cycle for decarboxylative arylation reaction.
Scheme 158: Ligand-free approach for arylation of imidazo[1,2-a]pyridine-3-carboxylic acids.
Scheme 159: Mechanism for ligandless arylation reaction.
Scheme 160: NHC-Pd(II) complex assisted arylation reaction.
Scheme 161: C-3 arylation of imidazo[1,2-a]pyridines with aryl bromides catalyzed by Pd(OAc)2.
Scheme 162: Pd(II)-catalyzed C-3 arylations with aryl tosylates and mesylates.
Scheme 163: CDC reaction for the synthesis of imidazo[1,2-a]pyridines.
Scheme 164: Plausible reaction mechanism for Pd(OAc)2-catalyzed synthesis of imidazo[1,2-a]pyridines.
Scheme 165: Pd-catalyzed C–H amination reaction.
Scheme 166: Mechanism for C–H amination reaction.
Scheme 167: One-pot synthesis for 3,6-di- or 2,3,6-tri(hetero)arylimidazo[1,2-a]pyridines.
Scheme 168: C–H/C–H cross-coupling reaction of IPs and azoles catalyzed by Pd(II).
Scheme 169: Mechanistic cycle.
Scheme 170: Rh-catalyzed C–H arylation reaction.
Scheme 171: Mechanistic pathway for C–H arylation of imidazo[1,2-a]pyridine.
Scheme 172: Rh(III)-catalyzed double C–H activation of 2-phenylimidazo[1,2-a]pyridines and alkynes.
Scheme 173: Rh(III)-catalyzed mechanistic pathway.
Scheme 174: Rh(III)-mediated oxidative coupling reaction.
Scheme 175: Reactions showing functionalization of the product obtained by the group of Kotla.
Scheme 176: Mechanism for Rh(III)-catalyzed oxidative coupling reaction.
Scheme 177: Rh(III)-catalyzed C–H activation reaction.
Scheme 178: Mechanistic cycle.
Scheme 179: Annulation reactions of 2-arylimidazo[1,2-a]pyridines and alkynes.
Scheme 180: Two-way reaction mechanism for annulations reaction.
Scheme 181: [RuCl2(p-cymene)]2-catalyzed C–C bond formation reaction.
Scheme 182: Reported reaction mechanism.
Scheme 183: Fe(III) catalyzed C-3 formylation approach.
Scheme 184: SET mechanism-catalyzed by Fe(III).
Scheme 185: Ni(dpp)Cl2-catalyzed KTC coupling.
Scheme 186: Pd-catalyzed SM coupling.
Scheme 187: Vanadium-catalyzed coupling of IP and NMO.
Scheme 188: Mechanistic cycle.
Scheme 189: Selective C3/C5–H bond functionalizations by mono and bimetallic systems.
Scheme 190: rGO-Ni@Pd-catalyzed C–H bond arylation of imidazo[1,2-a]pyridine.
Scheme 191: Mechanistic pathway for heterogeneously catalyzed arylation reaction.
Scheme 192: Zinc triflate-catalyzed coupling reaction of substituted propargyl alcohols.
Amine–borane complex-initiated SF5Cl radical addition on alkenes and alkynes
- Audrey Gilbert,
- Pauline Langowski,
- Marine Delgado,
- Laurent Chabaud,
- Mathieu Pucheault and
- Jean-François Paquin
Beilstein J. Org. Chem. 2020, 16, 3069–3077, doi:10.3762/bjoc.16.256
Graphical Abstract
Scheme 1: Dolbier’s protocol for the SF5Cl radical addition on alkenes.
Scheme 2: Proposed mechanism for the amine–borane complex-initiated radical addition of SF5Cl on alkenes.
Figure 1: Structures and acronyms of the amine-borane complexes investigated.
Scheme 3: Scope of the Et3B and the DICAB-initiated SF5Cl additions on alkenes. Unless noted otherwise, isola...
Scheme 4: Scope of the Et3B and the DICAB-initiated SF5Cl additions on alkynes. Unless noted otherwise, isola...
Recent advancements in the synthesis of Veratrum alkaloids
- Morwenna Mögel,
- David Berger and
- Philipp Heretsch
Beilstein J. Org. Chem. 2025, 21, 2657–2693, doi:10.3762/bjoc.21.206
Graphical Abstract
Scheme 1: Representatives of steroid alkaloid classes. Marked in blue is the steroidal cholestane framework, ...
Scheme 2: Subclasses of Veratrum alkaloids: jervanine, veratramine and cevanine-type [8].
Scheme 3: Flow chart presentation of the synthesis of (−)-englerin A developed by the Christmann group [10].
Scheme 4: Structures and year of synthesis of the three types of Veratrum alkaloids reported in the literatur...
Scheme 5: Key step in the synthesis of cyclopamine (6) by the Giannis group [21].
Scheme 6: Overview of the semisynthesis of cyclopamine (6) reported by the Giannis group in 2009 [21].
Scheme 7: Key steps in the synthesis of cyclopamine (6) by the Baran group [23].
Scheme 8: Overview of the total synthesis of cyclopamine (6) by the Baran group in 2023 [23].
Scheme 9: Key steps in the synthesis of cyclopamine (6) by the Zhu/Gao group [25].
Scheme 10: Overview of the total synthesis of cyclopamine (6) by the group of Zhao/Gao in 2023 [25].
Scheme 11: Key steps in the synthesis of cyclopamine (6) by the Liu/Qin group [26].
Scheme 12: Overview of the semisynthesis of cyclopamine (6) by the Liu/Qin group in 2024 [26].
Scheme 13: Key steps in the synthesis of jervine (12) by the Masamune group [14].
Scheme 14: Overview of the total synthesis of jervine (12) by the Masamune group in 1968 [14].
Scheme 15: Color-coded schemes of the presented cyclopamine (6) syntheses by Giannis, Baran, Zhu/Gao, and Liu/...
Scheme 16: Key steps in the total synthesis of veratramine (13) by the Johnson group [15].
Scheme 17: Overview of the total synthesis of veratramine (13) by the Johnson group in 1967 [15].
Scheme 18: Key steps in the synthesis of veratramine (13) by the Zhu/Gao group [25].
Scheme 19: Shortened overview of the total synthesis of veratramine (13) by the Zhu/Gao group in 2023 [25].
Scheme 20: Key steps in the synthesis of veratramine by the Liu/Qin group [26].
Scheme 21: Overview of the semisynthesis of veratramine (13) by the Liu/Qin group in 2024 [26].
Scheme 22: Key steps in the synthesis of veratramine (13) by the Trauner group [27].
Scheme 23: Overview of the total synthesis of veratramine (13) by the Trauner group in 2025 [27].
Scheme 24: Key steps in the synthesis of verarine (14) by the Kutney group [16-19].
Scheme 25: Overview of the total synthesis of verarine (14) by the Kutney group reported 1962–1968 [16-19].
Scheme 26: Color-coded schemes of the presented veratramine-type alkaloid synthesis of Zhu/Gao, Liu/Qin and Tr...
Scheme 27: Structures of veracevine (86), veratridine (87), and cevadine (88).
Scheme 28: Key step in the semisynthesis of verticine (15) by the Kutney group (1977) [20,46].
Scheme 29: Overview of the semisynthesis of verticine (15) by the Kutney group (1977) [20,46].
Scheme 30: Key step of the total synthesis of (±)-4-methylenegermine (17) by the Stork group (2017) [22].
Scheme 31: Overview of the total synthesis of (±)-4-methylenegermine (17) by the Stork group (2017) [22].
Scheme 32: Key step of the total synthesis of heilonine (16) by Cassaidy and Rawal (2021) [24].
Scheme 33: Overview of the total synthesis of heilonine (16) by Cassaidy and Rawal (2021) [24]. FGI: functional gr...
Scheme 34: Key steps of the synthesis of heilonine (16) by Dai and co-workers (2024) [28].
Scheme 35: Overview of the total synthesis of heilonine (16) by Dai and co-workers (2024) [28].
Scheme 36: Key steps of the total synthesis of zygadenine (18) reported by Luo and co-workers [29].
Scheme 37: Overview of the total synthesis of zygadenine (18) by Luo and co-workers (2023) [29].
Scheme 38: Key step of the divergent total syntheses of highly oxidized cevanine-type alkaloids by Luo and co-...
Scheme 39: Divergent syntheses of highly oxidized cevanine-type alkaloids by Luo and co-workers (2024) [30].
Scheme 40: Color-coded overview of the presented cevanine-type alkaloid syntheses [10,20,22,24,28-30,46]. LLS: longest linear sequen...
A mild and atom-efficient four-component cascade strategy for the construction of biologically relevant 4-hydroxyquinolin-2(1H)-one derivatives
- Dmitrii A. Grishin,
- Kseniia I. Sharkovskaia,
- Ilya G. Kolmakov,
- Daria A. Ipatova,
- Rostislav A. Petrov,
- Nikolai D. Dagaev,
- Dmitry A. Skvortsov,
- Maria G. Khrenova,
- Valeriy V. Andreychev,
- Sergei A. Evteev,
- Yan A. Ivanenkov,
- Roman L. Antipin,
- Olga А. Dontsova and
- Elena K. Beloglazkina
Beilstein J. Org. Chem. 2026, 22, 244–256, doi:10.3762/bjoc.22.18
Graphical Abstract
Figure 1: Examples of biologically active quinolin-2(1H)-ones.
Figure 2: Structures obtained via rational design aimed at enhancing antibacterial activity.
Scheme 1: Previously reported and newly developed 3-(4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)-3-arylpropanoi...
Scheme 2: Retrosynthetic analysis: two alternative approaches to target compounds.
Scheme 3: Two-stage synthesis A) and one-stage one-pot synthesis B) of 6-halogen-4-hydroxyquinoline-2(1H)-one...
Scheme 4: Previous synthetic attempts toward the target chemotype using various approaches.
Scheme 5: Four-component synthesis of 3-(6-halo-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)-3-(3,4-dimethoxyphe...
Scheme 6: The proposed mechanism of the four-component reaction.
Scheme 7: Synthesis of isopropyl (12a–c) and cyclohexyl (13а–с) esters of 3-(4-hydroxy-2-oxo-1,2-dihydroquino...
Figure 3: In vitro antibacterial activity studies. А) In vitro antibacterial activity using the E. coli ΔtolC...
Synthetic approaches to bowl-shaped π-conjugated sumanene and its congeners
- Shakeel Alvi and
- Rashid Ali
Beilstein J. Org. Chem. 2020, 16, 2212–2259, doi:10.3762/bjoc.16.186
Graphical Abstract
Figure 1: Representation of corannulene (1) and sumanene (2), the subunits of fullerene (C60).
Scheme 1: Mehta’s unsuccessful effort for the synthesis of sumanene scaffold 2.
Scheme 2: First synthesis of sumanene 2 by Sakurai et al. from norbornadiene 10.
Scheme 3: Synthesis of trimethylsumanene 28 from easily accessible norbornadiene (10).
Scheme 4: Generation of anions 29–31 and the preparation of tris(trimethylsilyl)sumanene 32.
Scheme 5: Synthesis of tri- and hexa-substituted sumanene derivatives.
Scheme 6: Synthesis of bowl-shaped π-extended sumanene derivatives 37a–f.
Scheme 7: Synthesis of monooxasumanene 38, trioxosumanene 40 along with imination of them.
Scheme 8: Synthesis of trimethylsumanenetrione 46 and exo-functionalized products 45a,b.
Scheme 9: Synthesis of bisumanenylidene 47 and sumanene dimer 48 from 2.
Scheme 10: The mono-substitution of 2 to generate diverse mono-sumanene derivatives 49a–d.
Scheme 11: Synthesis of sumanene building block 53 useful for further extension.
Scheme 12: Synthesis of hexafluorosumanene derivative 55 by Sakurai and co-workers.
Scheme 13: Preparation of sumanene-based carbene 60 and its reaction with cyclohexane.
Scheme 14: Barton–Kellogg reaction for the synthesis of sterically hindered alkenes.
Scheme 15: Synthesis of hydroxysumanene 68 by employing Baeyer–Villiger oxidation.
Scheme 16: Synthesis of sumanene derivatives having functionality at an internal carbon.
Scheme 17: Mechanism for nucleophilic substitution reaction at the internal carbon.
Scheme 18: Synthesis of diverse monosubstituted sumanene derivatives.
Scheme 19: Synthesis of di- and trisubstituted sumanene derivatives from sumanene (2).
Scheme 20: Preparation of monochlorosumanene 88 and hydrogenation of sumanene (2).
Scheme 21: The dimer 90 and bissumanenyl 92 achieved from halosumannes.
Scheme 22: Pyrenylsumanene 93 involving the Suzuki-coupling as a key transformation.
Scheme 23: Synthesis of various hexaarylsumanene derivatives using the Suzuki-coupling reaction.
Scheme 24: Synthesis of hexasubstituted sumanene derivatives 96 and 97.
Scheme 25: Synthesis of thioalkylsumanenes via an aromatic nucleophilic substitution reaction.
Scheme 26: Synthesis of tris(ethoxycarbonylethenyl)sumanene derivative 108.
Scheme 27: Synthesis of ferrocenyl-based sumanene derivatives.
Scheme 28: Synthesis of sumanenylferrocene architectures 118 and 119 via Negishi coupling.
Scheme 29: Diosmylation and the synthesis of phenylboronate ester 121 of sumanene.
Scheme 30: Synthesis of the iron-complex of sumanene.
Scheme 31: Synthesis of tri- and mononuclear sumanenyl zirconocene complexes.
Scheme 32: Synthesis of [CpRu(η6-sumanene)]PF6.
Scheme 33: Preparation of sumanene-based porous coordination networks 127 (spherical tetramer units) and 128 (...
Scheme 34: Synthesis of sumanenylhafnocene complexes 129 and 130.
Scheme 35: Synthesis of 134 and 135 along with PdII coordination complex 136.
Scheme 36: Synthesis of alkali metals sumanene complex K7(C21H102−)2(C21H93−)·8THF (137) containing di- and tr...
Scheme 37: The encapsulation of a Cs+ ion between two sumanenyl anions.
Scheme 38: Synthesis of monothiasumanene 140 and dithiasumanene 141 from 139.
Scheme 39: Synthesis of trithiasumanene 151 by Otsubo and his co-workers.
Scheme 40: Synthesis of trithiasumanene derivatives 155 and 156.
Scheme 41: Synthetic route towards hexathiolated trithiasumanenes 158.
Scheme 42: Synthesis of triselenasumanene 160 by Shao and teammates.
Scheme 43: Synthesis of tritellurasumanene derivatives from triphenylene skeletons.
Scheme 44: Synthesis of pyrazine-fused sumanene architectures through condensation reaction.
Scheme 45: Treatment of the trichalcogenasumanenes with diverse oxidative reagents.
Scheme 46: Ring-opening reaction with H2O2 and oxone of heterasumanenes 178 and 179.
Scheme 47: Synthesis of polycyclic compounds from sumanene derivatives.
Scheme 48: Synthesis of diimide-based heterocycles reported by Shao’s and co-workers.
Scheme 49: Synthesis of pristine trichalcogenasumanenes, 151, 205, and 206.
Scheme 50: Synthesis of trichalcogenasumanenes via hexaiodotriphenylene precursor 208.
Scheme 51: Synthesis of trisilasumanenes 214 and 215.
Scheme 52: Synthesis of trisilasumanene derivatives 218 and 219.
Scheme 53: Synthesis of novel trigermasumanene derivative 223.
Scheme 54: An attempt towards the synthesis of tristannasumanene derivative 228.
Scheme 55: Synthesis of triphosphasumanene trisulfide 232 from commercially available 229.
Scheme 56: The doping of sumanene derivatives with chalcogens (S, Se, Te) and phosphorus.
Scheme 57: Synthesis of heterasumanene containing three different heteroatoms.
Scheme 58: Synthesis of trichalcogenasumanene derivatives 240 and 179.
Scheme 59: Preparation of trichalcogenasumanenes 245 and 248.
Scheme 60: Design and synthesis of trichalcogenasumanene derivatives 252 and 178.
Scheme 61: Synthesis of spirosumanenes 264–269 and non-spiroheterasumanenes 258–263.
Scheme 62: Synthesis of sumanene-type hetero polycyclic compounds.
Scheme 63: Synthesis of triazasumanenes 288 and its sulfone congener 287.
Scheme 64: Synthesis of C3-symmetric chiral triaryltriazasumanenes via cross-coupling reaction.
Scheme 65: Synthesis of mononaphthosumanene 293 using Suzuki coupling as a key step.
Scheme 66: Synthesis of di- and trinaphthosumanene derivatives 302–304.
Scheme 67: Synthesis of hemifullerene skeletons by Hirao’s group.
Scheme 68: Design and construction of C70 fragment from a C60 sumanene fragment.
Ring contraction and ring expansion reactions in terpenoid biosynthesis and their application to total synthesis
- Nicolas Kratena,
- Nicolas Heinzig and
- Peter Gärtner
Beilstein J. Org. Chem. 2026, 22, 289–343, doi:10.3762/bjoc.22.21
Graphical Abstract
Scheme 1: Mechanistic overview of enzymes involved in ring-size-altering reactions: A: Difference in ionisati...
Scheme 2: A: Ring contraction through involvement of carbocationic intermediates in thujane monoterpene biosy...
Scheme 3: Examples of concerted ring expansions of carbocation intermediates in PxaTPS8-catalysed cyclisation...
Scheme 4: Sequential ring expansions during astellifadiene (17) synthesis reported by Abe and co-workers.
Scheme 5: Cyclobutane ring expansion and sequential ring contractions catalysed by the synthase AITS in the b...
Scheme 6: Ring expansion and transannular ring contraction of a cyclopentane to cyclobutane in the biosynthes...
Scheme 7: Computationally elucidated concerted cyclisations/alkyl/hydride shifts during the biosynthesis of t...
Scheme 8: Cyclisation events and 6→5-ring contraction during the construction of epi-isozizaene (26) catalyse...
Scheme 9: Transannular cyclisations and 4→5-membered ring expansion through dyotropic 1,2-rearrangement of al...
Scheme 10: Ring expansion in presilphiperfolan-8b-ol (31) biosynthesis and ring contraction of the presilphipe...
Scheme 11: Ring contraction via transannular cyclopropanation and opening of cyclopropane in the biosynthesis ...
Scheme 12: The crucial CYP450-catalysed oxidative rearrangement defining the skeleton in gibberellin biosynthe...
Scheme 13: CYP450-mediated oxidation of cyclopentane methylene expanding the 8-membered ring in the biosynthes...
Scheme 14: CYP450-mediated oxidation of an exocyclic methyl group to effect transannular cyclisation across th...
Scheme 15: Non-enzymatic transannular aldol reaction enables the formation of the 5/13/3-tricyclic ring system...
Scheme 16: A: Oxidative ring expansion of a cyclopentane by incorporation of a methyl group in the biosynthesi...
Scheme 17: Rearrangement and ring expansion in the construction of the complex bridged carbon framework of and...
Scheme 18: Ketoglutarate-mediated oxidations of preaustinoid A1 (53) en route to complex meroterpenoids, B-rin...
Scheme 19: Proposed putative biosynthetic formation of the tigliane skeleton from an E,E,Z-triene.
Scheme 20: Photocatalytic tandem ring expansion/contraction of santonin to give photosantonin products and gua...
Scheme 21: A: Proposed biosynthesis of stelleroid B (66) from stelleranoid I (65) by ketol rearrangement; B: o...
Scheme 22: Singular examples of A,B-ring contractions and expansions in the biosynthesis of sesquiterpenoids e...
Scheme 23: A: plausible proposed biosynthetic pathway for the tigliane/ingenane skeletal rearrangement and 1,2...
Scheme 24: A: Multiple ring-size alterations during xenovulene A (90) biosynthesis; B: Ring contraction and re...
Scheme 25: Proposed biosyntheses of the complex, polycyclic terpenoid illisimonin A (97) and the bridged antro...
Scheme 26: Proposed biogenetic origin for the meroterpenoid liphagal (104) via epoxide-mediated ring expansion....
Scheme 27: Proposed biogenetic origin for the ring-contracted members of the taiwaniaquinol family.
Scheme 28: A: Schenck ene/Hock/Aldol cascade effecting B-ring contraction in atheronal B (113); B: Selective C...
Scheme 29: A: D-ring expansion of buxenone (118) via cyclopropanation towards buxaustroine A (119); B: Propose...
Scheme 30: Biosynthetic origin of alstoscholarinoids A (124) and B (125) via cascade oxidative rearrangement c...
Scheme 31: Biogenetic origin of the hedgehog signalling inhibitor cyclopamine (129) by tandem ring contraction...
Scheme 32: Proposed biogenetic origin of the B-ring contracted spirocyclic triterpenoid spirochensilide A (131...
Scheme 33: A: Proposed B-ring contraction during the biosynthesis of holophyllane A (133); B: B-ring contracti...
Scheme 34: Radical and ionic/polar mechanisms for the C-ring-contracted triterpenoids phomopsterone B (139) an...
Scheme 35: A: Plausible mechanism for the formation of schiglautone A (144) from anwuweizic acid (145); B: Pro...
Scheme 36: Reported biosynthetic proposal for the formation of B-ring expanded triterpenoids rhodoterpenoids A...
Scheme 37: A: Final reaction step in the synthesis of euphorikanin A (154), benzilic acid-type ring contractio...
Scheme 38: Tricyclic ring expansion in the Gui synthesis of gibbosterol A (158) and sarocladione (160) via Ru-...
Scheme 39: A: A-ring expansion during the Gui synthesis of rubriflordilactone B (161); B: Mechanism for the bi...
Scheme 40: Photosantonin rearrangement effects A/B ring contraction/expansion in Li’s synthesis of the complex...
Scheme 41: Tandem A/B ring expansion/contraction of an ergosterol derivative via pinacol rearrangement in the ...
Scheme 42: Synthetic studies towards cyclocitrinol (179) by A) the semisynthetic approach by Gui et al. using ...
Scheme 43: A: Bioinspired synthesis of spirochensilide A (131) by the Heretsch group via selective 8,9-epoxida...
Scheme 44: Baran’s synthesis of cortistatin A (191), expanding the B-ring through a cyclopropane fragmentation....
Scheme 45: Ding’s total synthesis of retigeranic acid (198) showcasing sequential 6→5 ring contractions.
Scheme 46: A: Oxa-di-π-methane (ODPM) rearrangement of a bicyclic ketone en route to silphiperfolenone (203); ...
Scheme 47: Biomimetic synthesis of liphagal (104) from sclareolide (221) by George and co-workers.
Scheme 48: Wu’s bioinspired synthesis of cucurbalsaminones B (224) and C (225) by photocatalytic oxa-di-π-meth...
Scheme 49: Baran’s total synthesis of maoecrystal V (230) featuring a pinacol rearrangement for ring expansion...
Scheme 50: A: Ketol rearrangement leading to ring contraction in the total synthesis of preaustinoid B; B: Ben...
Scheme 51: A: Scheidt’s synthesis of isovelleral (251) by pinacol rearrangement triggered by Mitsunobu conditi...
Scheme 52: Biomimetic transformations of simplified test substrates related to Euphorbia diterpenoids.
Scheme 53: A: First generation synthesis of taiwaniaquinones by benzilic acid-type rearrangement of the B-ring...
Scheme 54: A: Norrish type 1 radical recombination leading to ring contraction en route to cuparenone (272): 1...
Scheme 55: Ring contraction of a bridged D-ring system in the total synthesis of andrastatin D (280), terrenoi...
Scheme 56: Biomimetic synthesis of hyperjapone A (284) and hyperjaponol C (285) by George et al.
Scheme 57: Heretsch’ synthesis of dankastarones A (288) and B (289), swinhoeisterol A (290), and periconiaston...
Scheme 58: A: Zhang’s ring contraction during the synthesis of stemar-13-ene (295) by pinacol rearrangement; B...
Scheme 59: Trauner’s biomimetic synthesis of preuisolactone A (307) featuring a ring contraction via benzilic ...
Scheme 60: Bioinspired approaches for ring contraction/expansion reactions in the synthesis of alstoscholarino...
Scheme 61: A: Sarpong and Li, Wang and co-workers’ ring expansion of cephanolide A (313) to reach harringtonol...
Eosin Y-catalyzed visible-light-mediated aerobic oxidative cyclization of N,N-dimethylanilines with maleimides
- Zhongwei Liang,
- Song Xu,
- Wenyan Tian and
- Ronghua Zhang
Beilstein J. Org. Chem. 2015, 11, 425–430, doi:10.3762/bjoc.11.48
Graphical Abstract
Scheme 1: Visible-light-induced sp3 C–H bond functionalization of tertiary amines.
Scheme 2: Substrate scope for aerobic oxidative cyclization of N,N-dimethylanilines with maleimides.
Scheme 3: A proposed reaction mechanism.
Arene activation via π-bond localization: concepts and opportunities
- Paul Meiners,
- Julian J. Melder and
- Tobias Morack
Beilstein J. Org. Chem. 2026, 22, 257–273, doi:10.3762/bjoc.22.19
Graphical Abstract
Figure 1: Aromatic molecules as the foundation of modern molecular chemistry.
Figure 2: Arenes as springboards to three-dimensional chemical space and strategies toward arene activation v...
Figure 3: Structure and synthetic utilization of strained arenes; NICS: nucleus independent chemical shifts [26-28].
Figure 4: Bonding and reactivity of η2-coordinated aromatic systems [44,46].
Figure 5: Illustrative selection of η2-coordinating dearomatization agents; MeIm: N-methylimidazole, NHE: nor...
Figure 6: Preparation, lability and most stable linkage isomers of pentaammineosmium(II) complexes.
Scheme 1: Heteroatom-directed reactions of η2-arene complexes [45,50].
Figure 7: Latent functionality through transient metal binding.
Figure 8: Selective hydrogenation of η2-coordinated benzene to cyclohexene under ambient conditions [53,54].
Scheme 2: Synthesis and utilization of enantioenrichted Mo(η2-arene) complexes in enantioselective synthesis [55]....
Scheme 3: Synthesis of trisubstituted cyclohexenes from phenyl sulfones enabled by tungsten-mediated dearomat...
Scheme 4: Diels–Alder reactions of η2-arene complexes with alkenes and alkynes; NMM: N-methylmaleimide [64,65].
Scheme 5: Binding characteristics and pioneering examples of isolable η3-benzyl complexes.
Figure 9: Divergent functionalization of benzyl electrophiles leveraging η3-benzyl complexes toward benzylic ...
Scheme 6: p-Selective allylation of benzyl chlorides with allylstannanes and subsequent synthetic expansion o...
Figure 10: Strategies for para- and ortho-selective arene functionalization/dearomatization via η3-benzyl comp...
Scheme 7: Substrate-dependent ortho- and para-selective dearomatization of naphthyl chlorides and leveraging ...
Figure 11: η4-Arene coordination as an underexplored but promising pathway for arene activation [96,98-100].
Chiral phosphines in nucleophilic organocatalysis
- Yumei Xiao,
- Zhanhu Sun,
- Hongchao Guo and
- Ohyun Kwon
Beilstein J. Org. Chem. 2014, 10, 2089–2121, doi:10.3762/bjoc.10.218
Graphical Abstract
Figure 1: Cyclic chiral phosphines based on bridged-ring skeletons.
Figure 2: Cyclic chiral phosphines based on binaphthyl skeletons.
Figure 3: Cyclic chiral phosphines based on ferrocene skeletons.
Figure 4: Cyclic chiral phosphines based on spirocyclic skeletons.
Figure 5: Cyclic chiral phosphines based on phospholane ring skeletons.
Figure 6: Acyclic chiral phosphines.
Figure 7: Multifunctional chiral phosphines based on binaphthyl skeletons.
Figure 8: Multifunctional chiral phosphines based on amino acid skeletons.
Scheme 1: Asymmetric [3 + 2] annulations of allenoates with electron-deficient olefins, catalyzed by the chir...
Scheme 2: Asymmetric [3 + 2] annulations of allenoate and enones, catalyzed by the chiral binaphthyl-based ph...
Scheme 3: Asymmetric [3 + 2] annulations of N-substituted olefins and allenoates, catalyzed by the chiral bin...
Scheme 4: Asymmetric [3 + 2] annulations of 2-aryl-1,1-dicyanoethylenes with ethyl allenoate, catalyzed by th...
Scheme 5: Asymmetric [3 + 2] annulations of 3-alkylideneindolin-2-ones with ethyl allenoate, catalyzed by the...
Scheme 6: Asymmetric [3 + 2] annulations of 2,6-diarylidenecyclohexanones with allenoates, catalyzed by the c...
Scheme 7: Asymmetric [3 + 2] annulations of allenoate with alkylidene azlactones, catalyzed by the chiral bin...
Scheme 8: Asymmetric [3 + 2] annulations of C60 with allenoates, catalyzed by the chiral phosphine B6.
Scheme 9: Asymmetric [3 + 2] annulations of α,β-unsaturated esters and ketones with an allenoate, catalyzed b...
Scheme 10: Asymmetric [3 + 2] annulations of exocyclic enones with allenoates, catalyzed by the ferrocene-modi...
Scheme 11: Asymmetric [3 + 2] annulations of enones with an allenylphosphonate, catalyzed by the ferrocene-mod...
Scheme 12: Asymmetric [3 + 2] annulations of 3-alkylidene-oxindoles with ethyl allenoate, catalyzed by the fer...
Scheme 13: Asymmetric [3 + 2] annulations of dibenzylideneacetones with ethyl allenoate, catalyzed by the ferr...
Scheme 14: Asymmetric [3 + 2] annulations of trisubstituted alkenes with ethyl allenoate, catalyzed by the fer...
Scheme 15: Asymmetric [3 + 2] annulations of 2,6-diarylidenecyclohexanones with allenoates, catalyzed by the f...
Scheme 16: Asymmetric [3 + 2] annulations of α,β-unsaturated ketones with ethyl allenoates, catalyzed by the f...
Scheme 17: Asymmetric [3 + 2] annulations of α,β-unsaturated esters with allenoates, catalyzed by the ferrocen...
Scheme 18: Asymmetric [3 + 2] annulations of alkylidene azlactones with allenoates, catalyzed by the chiral sp...
Scheme 19: Asymmetric [3 + 2] annulations of α-trimethylsilyl allenones and electron-deficient olefins, cataly...
Scheme 20: Asymmetric [3 + 2] annulations of α,β-unsaturated ketones with an allenone, catalyzed by the chiral...
Scheme 21: Asymmetric [3 + 2] annulations of cyclic enones with allenoates, catalyzed by the chiral α-amino ac...
Scheme 22: Asymmetric [3 + 2] annulations of arylidenemalononitriles and analogues with an allenoate, catalyze...
Scheme 23: Asymmetric [3 + 2] annulations of α,β-unsaturated esters with an allenoate, catalyzed by the chiral...
Scheme 24: Asymmetric [3 + 2] annulations of 3,5-dimethyl-1H-pyrazole-derived acrylamides with an allenoate, c...
Scheme 25: Asymmetric [3 + 2] annulations of maleimides with allenoates, catalyzed by the chiral phosphine H10....
Scheme 26: Asymmetric [3 + 2] annulations of α-substituted acrylates with allenoate, catalyzed by the chiral p...
Scheme 27: Asymmetric [3 + 2] annulation of an N-tosylimine with an allenoate, catalyzed by the chiral phosphi...
Scheme 28: Asymmetric [3 + 2] annulations of N-tosylimines with an allenoate, catalyzed by the chiral phosphin...
Scheme 29: Asymmetric [3 + 2] annulations of N-tosylimines with an allenoate, catalyzed by the chiral phosphin...
Scheme 30: Asymmetric [3 + 2] annulations of N-diphenylphosphinoyl aromatic imines with butynoates, catalyzed ...
Scheme 31: Asymmetric [3 + 2] annulations of N-tosylimines with allenylphosphonates, catalyzed by the chiral p...
Scheme 32: Asymmetric [3 + 2] annulation of an N-tosylimine with an allenoate, catalyzed by the chiral phosphi...
Scheme 33: Asymmetric [3 + 2] annulations of N-diphenylphosphinoyl aromatic imines with allenoates (top), cata...
Scheme 34: Asymmetric [3 + 2] annulation of N-diphenylphosphinoylimines with allenoates, catalyzed by the chir...
Scheme 35: Asymmetric [3 + 2] annulation of an azomethine imine with an allenoate, catalyzed by the chiral pho...
Scheme 36: Asymmetric [3 + 2] annulations between α,β-unsaturated esters/ketones and 3-butynoates, catalyzed b...
Scheme 37: Asymmetric intramolecular [3 + 2] annulations of electron-deficient alkenes and MBH carbonates, cat...
Scheme 38: Asymmetric [3 + 2] annulations of methyleneindolinone and methylenebenzofuranone derivatives with M...
Scheme 39: Asymmetric [3 + 2] annulations of activated isatin-based alkenes with MBH carbonates, catalyzed by ...
Scheme 40: Asymmetric [3 + 2] annulations of maleimides with MBH carbonates, catalyzed by the chiral phosphine ...
Scheme 41: A series of [3 + 2] annulations of various activated alkenes with MBH carbonates, catalyzed by the ...
Scheme 42: Asymmetric [3 + 2] annulations of an alkyne with isatins, catalyzed by the chiral phosphine F1.
Scheme 43: Asymmetric [4 + 2] annulations catalyzed by the chiral phosphine B1.
Scheme 44: Asymmetric [4 + 2] annulations catalyzed by the chiral phosphine H5.
Scheme 45: Asymmetric [4 + 2] annulations catalyzed by the chiral phosphines H13 and H12.
Scheme 46: Asymmetric [4 + 2] annulations catalyzed by the chiral phosphine H6.
Scheme 47: Kerrigan’s [2 + 2] annulations of ketenes with imines, catalyzed by the chiral phosphine B7.
Scheme 48: Asymmetric [4 + 1] annulations, catalyzed by the chiral phosphine G6.
Scheme 49: Asymmetric homodimerization of ketenes, catalyzed by the chiral phosphine F5 and F6.
Scheme 50: Aza-MBH/Michael reactions, catalyzed by the chiral phosphine G1.
Scheme 51: Tandem RC/Michael additions, catalyzed by the chiral phosphine H14.
Scheme 52: Intramolecular tandem RC/Michael addition, catalyzed by the chiral phosphine H15.
Scheme 53: Double-Michael addition, catalyzed by the chiral aminophosphine G9.
Scheme 54: Tandem Michael addition/Wittig olefinations, mediated by the chiral phosphine BIPHEP.
Scheme 55: Asymmetric Michael additions, catalyzed by the chiral phosphines H7, H8, and H9.
Scheme 56: Asymmetric γ-umpolung additions, catalyzed by the chiral phosphine A1.
Scheme 57: Asymmetric γ-umpolung additions, catalyzed by the chiral phosphines E2 and E3.
Scheme 58: Intramolecular γ-additions of hydroxy-2-alkynoates, catalyzed by the chiral phosphine D2.
Scheme 59: Intra-/intermolecular γ-additions, catalyzed by the chiral phosphine D2.
Scheme 60: Intermolecular γ-additions, catalyzed by the chiral phosphines B5 and B3.
Scheme 61: Intermolecular γ-additions, catalyzed by the chiral phosphines E6 and B4.
Scheme 62: Asymmetric allylic substitution of MBH acetates, catalyzed by the chiral phosphine G2.
Scheme 63: Allylic substitutions between MBH acetates or carbonates and an array of nucleophiles, catalyzed by...
Scheme 64: Asymmetric acylation of diols, catalyzed by the chiral phosphines E4 and E5.
Scheme 65: Kinetic resolution of secondary alcohols, catalyzed by the chiral phosphine E8 and E9.
Photocatalyzed elaboration of antibody-based bioconjugates
- Marine Le Stum,
- Eugénie Romero and
- Gary A. Molander
Beilstein J. Org. Chem. 2025, 21, 616–629, doi:10.3762/bjoc.21.49
Graphical Abstract
Figure 1: Representation of an antibody–drug conjugate. The antibody shown in this figure is from https://www...
Figure 2: a. Photoredox catalytic cycles; b. absorption spectrum of photosensitizers. Therapeutic window indi...
Figure 3: Graph representing the average number of publications focusing on photoredox chemistry applied to p...
Figure 4: Schematic procedure developed by Sato et al. on histidine photoinduced modification. The antibody s...
Figure 5: Schematic procedure of the divergent method developed by Sato et al. on histidine/tyrosine photoind...
Figure 6: Schematic procedure developed by Bräse et al. on photoinduced disulfide rebridging method.
Figure 7: Schematic procedure developed by Lang et al. on a photoinduced dual nickel photoredox-catalyzed app...
Figure 8: Schematic of the procedure developed by Chang et al. on photoinduced high affinity IgG Fc-binding s...
Figure 9: Potential advantages of photoredox chemistry for bioconjugation applied to antibodies. The antibody...
Figure 10: Representation of the photoinduced control of the DAR. The antibody shown in this figure is from ht...
Figure 11: Representation of a photoinduced control of multi-payloads ADC strategy. The antibody shown in this...
