Concept-driven strategies in target-oriented synthesis

• David Yu-Kai Chen,
• Chao Li and
• Yefeng Tang

Beilstein J. Org. Chem. 2026, 22, 451–454, doi:10.3762/bjoc.22.32

• -She Han and co-worker), bioinspired synthesis (review, Huilin Li, Xuegong She et al.), biosynthesis (fusicoccane diterpenoids, Yonghui Zhang, Ying Ye, Zheng Xiang et al.), chemoenzymatic synthesis (rhodexin A, Qianghui Zhou et al.)]; (ii) comparative analysis of target-oriented synthesis [complanadine

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

• . The ring enlargement is then proposedly initiated by protonation of the olefin giving rise to 101a, 1,2-alkyl shift to 101b and elimination to re-form the exocyclic olefin in 99. An elegant bioinspired synthesis of antroalbocin A (99) was reported by Kalesse using a photochemical rearrangement of a 5

• bioinspired synthesis (vide infra). The steroidal alkaloid cyclopamine (129), isolated from various species of the genus Veratrum exhibits rearranged C and D rings (see Scheme 31). From the more classical steroidal alkaloid solanidine (130), which is also present in the same species, a biosynthetic reaction

• applications of ring-size-altering reactions in natural product synthesis, regardless of biosynthetic relationship. In this section we aim to review examples in total and bioinspired synthesis which either closely resemble the proposed biosynthetic pathways, or which take inspiration from the principles that

Recent advances in total synthesis of illisimonin A

• Juan Huang and
• Ming Yang

Beilstein J. Org. Chem. 2025, 21, 2571–2583, doi:10.3762/bjoc.21.199

• total synthesis. Keywords: bioinspired synthesis; biosynthetic pathway; Illicium sesquiterpene; illisimonin A; total synthesis; Introduction The genus Illicium, the sole member of the family Illiciaceae, is a rich source of sesquiterpenoid natural products. To date, a wide variety of sesquiterpenes

• , albeit with a lower overall yield of 3%. Yang’s bioinspired synthesis of illisimonin A In 2023, Yang and co-workers reported a bioinspired divergent synthesis of illisimonin A and merrilactone A, which belonged to illisimonane-type and anislactone-type Illicium sesquiterpenes, respectively [30]. They

• biosynthetic pathway of illisimonin A. Yang’s bioinspired synthesis of illisimonin A. Dai’s asymmetric synthesis of (–)-illisimonin A. Lu’s total synthesis of illisimonin A. Initial efforts toward the total synthesis of illisimonin A by the Lu Group. Suzuki’s synthetic effort towards illisimonin A. Funding

Bioinspired total syntheses of natural products: a personal adventure

• Zhengyi Qin,
• Yuting Yang,
• Nuran Yan,
• Xinyu Liang,
• Zhiyu Zhang,
• Yaxuan Duan,
• Huilin Li and
• Xuegong She

Beilstein J. Org. Chem. 2025, 21, 2048–2061, doi:10.3762/bjoc.21.160

• ] (Figure 1). The bioinspired total synthesis literally showed the great power to gain complexity. In the 21st century, biomimetic or bioinspired synthesis has been widely realized as a powerful concept approach to natural product total synthesis, and a lot of total synthetic works of this kind have been

• supports the proposed biogenetic pathway, and the endo-selective stereochemical outcome of the Diels–Alder reaction in the bioinspired synthesis fully matched with the proposed approach in nature. Conclusion The biomimetic or bioinspired total synthesis of natural product has gone a long way from more than

• results than nature. Jia categorized their works into three sections to showcase how they learn from nature, including 1) to mimic the key cyclization steps, 2) to mimic the revised biosynthetic pathway proposed, and 3) to mimic the skeletal diversification process. These three types of bioinspired

Bioinspired total synthesis of katsumadain A by organocatalytic enantioselective 1,4-conjugate addition

• Yongguang Wang,
• Ruiyang Bao,
• Shengdian Huang and
• Yefeng Tang

Beilstein J. Org. Chem. 2013, 9, 1601–1606, doi:10.3762/bjoc.9.182

• neuraminidase (NA) inhibitor, was synthesized by using a bioinspired, organocatalytic enantioselective 1,4-conjugate addition of styryl-2-pyranone with cinnamaldehyde, followed by a tandem Horner–Wadsworth–Emmons/oxa Michael addition. Keywords: bioinspired synthesis; catalysis; katsumadain A; natural product