二萜生物碱全合成研究进展

doi:10.6023/cjoc202408012

摘要/Abstract

二萜生物碱是一类具有复杂化学结构和丰富生物活性的天然产物. 长期以来, 二萜生物碱独特的笼状骨架、多立体手性中心和稠密的含氧取代基团使其成为天然产物全合成领域的挑战性目标分子. 近五年, 该领域的研究取得了显著进展. 综述了2020年至今报道的二萜生物碱全合成工作, 重点介绍创新合成方法和策略的发展与应用.

关键词: 二萜生物碱, 天然产物, 全合成, 合成方法与策略

Diterpenoid alkaloids are a family of natural products with complex chemical structures and a rich array of biological activities. Their unique cage-like skeletons, multiple stereogenic chiral centers, and densely oxygenated substituents have long rendered them challenging target molecules in the field of total synthesis of natural product. In the past five years, significant progress has been made in this research area. The total synthesis of diterpenoid alkaloids reported from 2020 to the present is reviewed, focusing on the development and application of innovative synthetic methods and strategies.

Key words: diterpenoid alkaloid, natural product, total synthesis, synthetic method and strategy

引用此文

李闯, 张成, 刘小宇, 秦勇. 二萜生物碱全合成研究进展[J]. 有机化学, 2025, 45(3): 881-895.

Chuang Li, Cheng Zhang, Xiaoyu Liu, Yong Qin. Recent Progress in the Total Synthesis of Diterpenoid Alkaloids[J]. Chinese Journal of Organic Chemistry, 2025, 45(3): 881-895.

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图/表 22

图1. 二萜生物碱的结构分类

Figure 1. Structure classification of the diterpenoid alkaloids

图2. 2020~2024年间二萜生物碱全合成进展

Figure 2. Progress in the total synthesis of diterpenoid alkaloids during 2020~2024

图式1. (±)-Liangshanone的逆合成

Scheme 1. Retrosynthesis of (±)-liangshanone

图式2. (±)-Liangshanone的全合成

Scheme 2. Total synthesis of (±)-liangshanone

图式3. (–)-Napelline的逆合成

Scheme 3. Retrosynthesis of (–)-napelline

图式4. 纳哌林型二萜生物碱六环骨架的合成

Scheme 4. Synthesis of the hexacyclic skeleton of napelline-type diterpenoid alkaloids

图式5. 8个纳哌林型生物碱的全合成

Scheme 5. Completion of the synthesis of eight napelline-type alkaloids

图式6. (+)-Talassimidine和(+)-talassamine的逆合成

Scheme 6. Retrosynthesis of (+)-talassimidine and (+)-talassamine

图式7. (+)-Talassimidine和(+)-talassamine的全合成

Scheme 7. Total synthesis of (+)-talassimidine and (+)-talassamine

图式8. (+)-Davisinol和(+)-18-benzoyldavisinol的逆合成

Scheme 8. Retrosynthesis of (+)-davisinol and (+)-18-benzoyldavisinol

图式9. (+)-Davisinol和(+)-18-benzoyldavisinol的全合成

Scheme 9. Total synthesis of (+)-davisinol and (+)-18-benzoyldavisinol

图式10. (–)-Garryine的逆合成

Scheme 10. Retrosynthesis of (–)-garryine

图11. (–)-Garryine的全合成

Scheme 11. Total synthesis of (–)-garryine

图式12. (±)-Talatisamine的逆合成

Scheme 12. Retrosynthesis of (±)-talatisamine

图式13. (±)-Talatisamine的全合成

Scheme 13. Total synthesis of (±)-talatisamine

图式14. (–)-Talatisamine, (–)-liljestrandisine和(–)-liljestrandine的逆合成

Scheme 14. Retrosynthesis of (–)-talatisamine, (–)-liljestrandisine, and (–)-liljestrandine

图式15. 手性五环中间体126的合成

Scheme 15. Synthesis of chiral pentacyclic intermediate 126

图式16. (–)-Talatisamine, (–)-liljestrandisine和–)-liljestrandine的全合成

Scheme 16. Total synthesis of (–)-talatisamine, (–)-liljestrandisine, and (–)-liljestrandine

图式17. (±)-Puberuline C的逆合成

Scheme 17. Retrosynthesis of (±)-puberuline C

图式18. (±)-Puberuline C的全合成

Scheme 18. Total synthesis of (±)-puberuline C

图式19. (±)-Vilmoraconitine的逆合成

Scheme 19. Retrosynthesis of (±)-vilmoraconitine

图式20. (±)-Vilmoraconitine的全合成

Scheme 20. Total synthesis of (±)-vilmoraconitine

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