Synthesis and biological evaluation of new brassinosteroid analogs with C-22 benzoate function

• María Núñez,
• Camila Escobar,
• Mario Párraga,
• Mauricio Soto,
• Luis Espinoza-Catalán,
• Katy Díaz and
• Andrés F. Olea

Beilstein J. Org. Chem. 2026, 22, 753–762, doi:10.3762/bjoc.22.57

• . Keywords: biological activity; brassinosteroids; BRI1-EMS-Suppressor1; ligand–receptor interaction; structure–activity relationship; Introduction Brassinosteroids (BRs) are phytohormones that are widespread in the plant kingdom, and are found in very low concentrations, i.e., in the of nano- to micromolar

• of the signaling process. Structures of natural occurring brassinosteroids. Structures of C-22 benzoate-functionalized brassinosteroid analogs 4–14 and 17–22 prepared from the known precursor 16 [29], analog 16a [29] and structure of starting material 23,24-bisnor-5-cholenic acid 3β-acetate (15

Cytochrome P450 monooxygenase-mediated tailoring of triterpenoids and steroids in plants

• Karan Malhotra and
• Jakob Franke

Beilstein J. Org. Chem. 2022, 18, 1289–1310, doi:10.3762/bjoc.18.135

• ], cosmetics [3] and pharmaceutical industries [4]. Plant triterpenoids include primary metabolites such as phytosterols or steroidal hormones such as brassinosteroids, but also specialised metabolites that convey diverse biological functions [5]. A key factor for the structural richness of triterpenoids and

Synthesis of ergostane-type brassinosteroids with modifications in ring A

• Vladimir N. Zhabinskii,
• Darya A. Osiyuk,
• Yuri V. Ermolovich,
• Natalia M. Chaschina,
• Tatsiana S. Dalidovich,
• Miroslav Strnad and
• Vladimir A. Khripach

Beilstein J. Org. Chem. 2017, 13, 2326–2331, doi:10.3762/bjoc.13.229

• ,3α-, and 2β,3β-dihydroxy-, 3-keto-, 3α- and 3β-hydroxy-, 2α-hydroxy-3-keto-) were synthesized from 2α,3α-diols in a few simple steps (Corey–Winter reaction, epoxidation, oxidation, hydride reduction, etc.). Keywords: biosynthetic precursors; brassinosteroids; diols; epibrassinolide; epicastasterone

• ; metabolites; Introduction The group of steroid plant hormones called brassinosteroids (BS) currently comprises about 70 compounds [1]. It is generally accepted that only few of them (such as brassinolide, castasterone, epibrassinolide, etc.), possessing 2α,3α-, (22R,23R)-diol groups, B-lactone, and 6-ketone

• developed a new strategy for synthesizing minor constituents of the class of BS phytohormones which is based on the use of readily available brassinosteroids of this class. Its advantage is that it allows preparing a full set of A-ring units (Δ2-, 2α,3α- and 2β,3β-epoxy-, 2α,3β-, 2β,3α-, and 2β,3β-dihydroxy

Cross-metathesis of allylcarboranes with O-allylcyclodextrins

• Ivan Šnajdr,
• Zbyněk Janoušek,
• Jindřich Jindřich and
• Martin Kotora

Beilstein J. Org. Chem. 2010, 6, 1099–1105, doi:10.3762/bjoc.6.126

• synthesis of perfluoroalkylated analogs of brassinosteroids [5], 17α-perfluoroalkylestradiols [6], perfluoroalkylcyclodextrins [7], and perfluoroalkylcarboranes [8]. Successful execution of these reactions prompted us to study also cross-metathesis of allylcarboranes with O-allylcyclodextrins as a route to