Recent Progress in the Total Synthesis of Diterpenoid Alkaloids

doi:10.6023/cjoc202408012

Abstract

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

Cite this article

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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Fig. & Tab. 22

Figure 1. Structure classification of the diterpenoid alkaloids

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

Scheme 1. Retrosynthesis of (±)-liangshanone

Scheme 2. Total synthesis of (±)-liangshanone

Scheme 3. Retrosynthesis of (–)-napelline

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

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

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

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

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

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

Scheme 10. Retrosynthesis of (–)-garryine

Scheme 11. Total synthesis of (–)-garryine

Scheme 12. Retrosynthesis of (±)-talatisamine

Scheme 13. Total synthesis of (±)-talatisamine

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

Scheme 15. Synthesis of chiral pentacyclic intermediate 126

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

Scheme 17. Retrosynthesis of (±)-puberuline C

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

Scheme 19. Retrosynthesis of (±)-vilmoraconitine

Scheme 20. Total synthesis of (±)-vilmoraconitine

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