Recent Advance in the Synthesis of Tricyclic Marine Alkaloids: Cylindricines, Lepadiformines, and Fasicularin

doi:10.6023/cjoc202410006

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (3): 837-851.DOI: 10.6023/cjoc202410006 Previous Articles Next Articles

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三环海洋生物碱Cylindricines/Lepadiformines/Fasicularin的合成进展

李芸杉^a^,^b, 张钰欣^a, 唐叶峰^a^,^*()

a 清华大学药学院北京生物结构前沿研究中心生命有机磷化学及化学生物学教育部重点实验室北京 100084
b 重庆大学药学院创新药物研究中心重庆 401331

收稿日期:2024-10-12 修回日期:2024-12-01 发布日期:2024-12-19
基金资助:
国家自然科学基金(22271172); 国家自然科学基金(22471139)

Recent Advance in the Synthesis of Tricyclic Marine Alkaloids: Cylindricines, Lepadiformines, and Fasicularin

Yunshan Li^a^,^b, Yuxin Zhang^a, Yefeng Tang^a()

a MOE Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology, Beijing Advanced Innovation Center for Structural Biology, School of Pharmaceutical Sciences, Tsinghua University, Beijing 100084
b Innovative Drug Research Center, School of Pharmaceutical Sciences, Chongqing University, Chongqing 401331

Received:2024-10-12 Revised:2024-12-01 Published:2024-12-19
Contact: * E-mail: yefengtang@tsinghua.edu.cn
Supported by:
National Natural Science Foundation of China(22271172); National Natural Science Foundation of China(22471139)

Cylindricines, lepadiformines and fasicularin consititute a small class of tricyclic marine alkaloids featuring a perhydropyrrolo[2,1-j]quinolines (6/6/5) or perhydropyrido[2,1-j]quinolines (6/6/6) core skeleton. These natural products possess novel chemical structures and exhibit a wide range of biological activities, thus attracting significant interest from synthetic chemists over the past four decades. The recent advance in the synthesis of this unique class of natural products since 2017 is summarized, focusing on the key steps that enable the assembly of their tricyclic skeletons.

Key words: alkaloid, marine natural product, total synthesis

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Yunshan Li, Yuxin Zhang, Yefeng Tang. Recent Advance in the Synthesis of Tricyclic Marine Alkaloids: Cylindricines, Lepadiformines, and Fasicularin[J]. Chinese Journal of Organic Chemistry, 2025, 45(3): 837-851.

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Fig. & Tab. 16

Figure 1. Representative tricyclic marine alkaloids

Scheme 1. Formal synthesis of (±)-lepadiformines A~C by Chiou’s group

Scheme 2. Synthesis of (±)-fasicularin by Chiou’s group

Scheme 3. Synthesis of (±)-cylindricine C by Back’s group

Scheme 4. Synthesis of (+)-cylindricine C by Chida’s group

Scheme 5. Synthesis of (-)-fasicularin by Chida’s group

Scheme 6. Synthesis of (-)-lepadiformines A, B and (+)-lepadiformine C by Gong’s group

Scheme 7. Formal synthesis of (–)-lepadiformines A, C and (–)-fasicularin by Toyooka’s group

Scheme 8. Synthesis of (–)-lepadiformine A by Tokuyama’s group

Scheme 9. Synthesis of (+)-cylindricines C, D, E by Huang’s group

Scheme 10. Synthesis of (–)-cylindricine H by Amat’s group

Scheme 11. Synthesis of (–)-lepadiformine A by Fuwa’s group

Scheme 12. Collective synthesis of cylindricines by Fuwa’s group

Scheme 13. Synthesis of (-)-fasicularin by Fuwa’s group

Scheme 14. Synthesis of (+)-cylindricine B by Smith’s group

Scheme 15. Synthesis of (–)-lepadiformine A, (+)-cylindricine C and (–)-fasicularin by Tang’s group

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三环海洋生物碱Cylindricines/Lepadiformines/Fasicularin的合成进展

Recent Advance in the Synthesis of Tricyclic Marine Alkaloids: Cylindricines, Lepadiformines, and Fasicularin

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Fig. & Tab. 16

References 19

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