Synthetic progress toward the marine natural product zamamiphidin A

Hao Wang; Di Tian; Zhaoxiang Meng; Zhihao Chen; Fei Xue; Xiao-Yu Liu; Hao Song; Yong Qin

doi:10.1039/d0ra01580f

Synthetic progress toward the marine natural product zamamiphidin A

RSC Adv. 2020 Mar 24;10(20):11903-11906. doi: 10.1039/d0ra01580f. eCollection 2020 Mar 19.

Authors

Hao Wang¹, Di Tian², Zhaoxiang Meng², Zhihao Chen², Fei Xue², Xiao-Yu Liu², Hao Song², Yong Qin²

Affiliations

¹ Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, School of Pharmaceutical Sciences, Chongqing University Chongqing 401331 P. R. China.
² Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, Sichuan Engineering Laboratory for Plant-Sourced Drug, Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University Chengdu 610041 P. R. China xuefei@scu.edu.cn yongqin@scu.edu.cn.

Abstract

An asymmetric synthetic approach to the octahydrofuro[3,4-b]pyridine framework of marine natural product zamamiphidin A has been described. The key steps include an asymmetric Michael addition of (R)-N-tert-butanesulfinyl imidate with enamidomalonate to install the C10 stereocenter, an intramolecular alkoxide exchange/Michael addition/hydrogenation sequence to construct the bicyclic ring system.