Asymmetric total synthesis of 3-epi-naucleamide A

doi:10.5246/jcps.2016.01.004

Journal of Chinese Pharmaceutical Sciences ›› 2016, Vol. 25 ›› Issue (1): 30-36.DOI: 10.5246/jcps.2016.01.004

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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).

Abstract

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

CLC Number:

R916

Supporting:

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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Asymmetric total synthesis of 3-epi-naucleamide A

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