A Practical Total Synthesis of (±)-Cermizine D and a Formal Synthesis of (±)-Cermizine C

Author:

Shi Xin123,Bao Ying123,Deng Zhen-Tao123,Zhu Yu23,Shao Li-Dong2,Zhang Hong-Bin1,Zhao Qin-Shi2

Affiliation:

1. Key Laboratory of Medicinal Chemistry for Natural Resources (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, P.R. China

2. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, P.R. China

3. University of Chinese Academy of Sciences, Beijing 100049, P.R. China

Abstract

A practical total synthesis of (±)-cermizine D and a formal synthesis of (±)-cermizine C were achieved. The four-step total synthesis comprised mainly a Michael addition, a Weinreb amide-activated substitution and a sequence of ketalation/PtO2-catalysed dearomatisation/reductive amination reactions that resulted in ring closure in 13.7% overall yield. The formal synthesis was accomplished in 29.7% overall yield.

Publisher

SAGE Publications

Subject

General Chemistry

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