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

• Original articles • Previous Articles     Next Articles

Asymmetric total synthesis of 3-epi-naucleamide A

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

  1. 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:

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: 

Supporting: