Progress in Total Syntheses of Dimeric Cyclotryptamine Alkaloids

doi:10.6023/cjoc201903058

Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (10): 2685-2704.DOI: 10.6023/cjoc201903058 Next Articles

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二聚环色胺生物碱的全合成研究进展

沈先福^a^b, 彭天凤^a, 周永云^b, 奚永开^b, 赵静峰^b, 羊晓东^b, 张洪彬^b^*()

^a 曲靖师范学院云贵高原化学功能材料与污染治理研究中心生物资源与食品工程学院云南曲靖 655011
^b 云南大学云南省天然产物转化与利用及教育部自然资源药物化学重点实验室昆明 650091

收稿日期:2019-03-26 修回日期:2019-04-18 发布日期:2019-05-10
通讯作者: 张洪彬 E-mail:zhanghb@ynu.edu.cn
基金资助:
长江学者和创新团队发展计划(IRT17R94);国家自然科学基金(2152197);国家自然科学基金(21861032);云南省自然科学基金(2018FD078);云南省自然科学基金(2017FH001-020);曲靖师范学院资助项目(2018QN002)

Progress in Total Syntheses of Dimeric Cyclotryptamine Alkaloids

Shen Xianfu^a^b, Peng Tianfeng^a, Zhou Yongyun^b, Xi Yongkai^b, Zhao Jingfeng^b, Yang Xiaodong^b, Zhang Hongbin^b^*()

^a Center for Yunnan-Guizhou Plateau Chemical Functional Materials and Pollution Control, College of Biological Resource and Food Engineering, Qujing Normal University, Qujing 655011, Yunnan
^b Key Laboratory of Natural Products Transformation and Utilization in Yunnan Province, Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education and Yunnan Province, Kunming 650091

Received:2019-03-26 Revised:2019-04-18 Published:2019-05-10
Contact: Zhang Hongbin E-mail:zhanghb@ynu.edu.cn
Supported by:
Project supported by the Program for Changjiang Scholars and Innovative Research Team in University(IRT17R94);The National Natural Science Foundation of China(2152197);The National Natural Science Foundation of China(21861032);The Natural Science Foundation of Yunnan Province(2018FD078);The Natural Science Foundation of Yunnan Province(2017FH001-020);The Qujing Normal University(2018QN002)

As interesting synthetic targets, dimeric cyclotryptamine alkaloids bearing sterically hindered vicinal all-carbon quaternary stereocenters have attracted significant attention from the synthetic community. Stereocontrolled synthesis of the congested all-carbon quaternary stereocenters in these alkaloids presents a formidable challenge. This review summarizes the synthetic efforts towards dimeric cyclotryptamine alkaloids in the last twelve years.

Key words: dimeric cyclotryptamine, alkaloids, vicinal quaternary carbons, oxindole, total synthesis

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Shen Xianfu, Peng Tianfeng, Zhou Yongyun, Xi Yongkai, Zhao Jingfeng, Yang Xiaodong, Zhang Hongbin. Progress in Total Syntheses of Dimeric Cyclotryptamine Alkaloids[J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2685-2704.

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Fig. & Tab. 29

Figure 1. Representative dimeric cyclotryptamine alkaloids

Scheme 1. Hypothesis for the biosynthesis of cyclotryptamine alkaloids

Scheme 2. Movassaghi’s synthetic route based on reductive dimerization

Scheme 3. Movassaghi’s synthetic route toward (—)-ditrypto- phenaline

Scheme 4. de Lera’s synthetic route toward (+)-WIN 64745

Scheme 5. Synthesis of (—)-chimonanthine by Ma’s group

. Peng’s synthetic route based on reductive dimerization Scheme 6

Scheme 7. Oguri’s synthetic route based on reductive dimerization

Scheme 8. Movassaghi’s synthetic route toward heterodimeric alkaloids

Scheme 9. Liang’s synthetic route toward (±)-folicanthine

Scheme 10. Ishikawa’s synthetic route based on oxidative dimerization

Scheme 11. Li’s synthetic route based on iodine mediated dimerization

Scheme 12. Bisai’s synthetic route toward (±)-folicanthine

Scheme 13. Xia’s synthetic route toward (—)-ditryptophenaline

Scheme 14. Xia’s synthetic route toward (+)-chimonanthine

Scheme 15. Zhang’s synthetic route toward (+)-chimonanthine

Scheme 16. Zhang’s synthetic route toward (—)-ditryptophenaline

Scheme 17. Kanai’s synthetic route based on asymmetric Michael additions

Scheme 18. Gong’s synthetic route toward (+)-folicanthine

Scheme 19. Zhang’s organo-catalyzed synthetic route

Scheme 20. Trost’s formal synthesis of (+)-ditryptophenaline and (—)-chimonanthine

Scheme 21. Bisai’s formal synthetic route

Scheme 22. Bisai’s formal synthesis of (+)-folicanthine

Scheme 23. Bisai’s formal synthesis of (—)-chimonanthine and (+)-calycanthine

Scheme 24. Ma’s formal synthetic route toward (+)-folicanthine

Scheme 25. Tu’s synthetic route based on asymmetric alkylations

Scheme 26. Shishido’s synthesis of (±)-folicanthine and (±)-chimonanthine

Scheme 27. Kawasaki’s synthetic route

Scheme 28. Bisai’s formal synthetic route

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二聚环色胺生物碱的全合成研究进展

Progress in Total Syntheses of Dimeric Cyclotryptamine Alkaloids

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Fig. & Tab. 29

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