3-epi-naucleamide A的不对称全合成

doi:10.5246/jcps.2016.01.004

中国药学(英文版) ›› 2016, Vol. 25 ›› Issue (1): 30-36.DOI: 10.5246/jcps.2016.01.004

3-epi-naucleamide A的不对称全合成

帕如克·艾毕布拉, 黄智, 付宏征^*, 贾彦兴^*

北京大学医学部药学院天然产物及仿生药物国家重点实验室, 北京 100191

收稿日期:2015-11-10 修回日期:2015-11-30 出版日期:2016-01-27 发布日期:2015-12-10
通讯作者: Tel.: 86-10-82805166, E-mail: yanxing_jia@bjmu.edu.cn
基金资助:
National Natural Science Foundation of China (Grant No. 21290183, and 21572008).

Asymmetric total synthesis of 3-epi-naucleamide A

Paruke Aibibula, Zhi Huang, Hongzheng Fu^*, Yanxing Jia^*

State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University Health Science Center, Beijing 100191, China

Received:2015-11-10 Revised:2015-11-30 Online:2016-01-27 Published:2015-12-10
Contact: Tel.: 86-10-82805166, E-mail: yanxing_jia@bjmu.edu.cn
Supported by:
National Natural Science Foundation of China (Grant No. 21290183, and 21572008).

摘要/Abstract

摘要：

本文尝试对由茜草科乌檀属植物中分离到的单萜吲哚生物碱进行集体合成研究, 以Evans辅基诱导的不对称共轭加成作为关键反应, 得到了H-15和H-3顺式的产物13, 并且通过官能团转化完成了3-epi-naucleamide A的不对称全合成。本研究的合成路线可应用于天然产物vincosamide的合成。

关键词: 单萜吲哚生物碱, Naucleamide A, 全合成

Abstract:

Attempts to collective synthesis of the monoterpene indole alkaloids, isolated from Nauclea species, were examined by using asymmetric conjugate addition with Evans’ chiral auxiliary as key step. However, only the H-15 and H-3 cis product 13 was obtained, which enabled us to achieve the asymmetric total synthesis of 3-epi-naucleamide A. The results indicate that this synthetic route can be applied in the synthesis of vincosamide.

Key words: Monoterpene indole alkaloids, Naucleamide A, Total synthesis

中图分类号:

R916

Supporting:

帕如克·艾毕布拉, 黄智, 付宏征, 贾彦兴. 3-epi-naucleamide A的不对称全合成[J]. 中国药学(英文版), 2016, 25(1): 30-36.

Paruke Aibibula, Zhi Huang, Hongzheng Fu, Yanxing Jia. Asymmetric total synthesis of 3-epi-naucleamide A[J]. Journal of Chinese Pharmaceutical Sciences, 2016, 25(1): 30-36.

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3-epi-naucleamide A的不对称全合成

Asymmetric total synthesis of 3-epi-naucleamide A

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