Efficient Synthesis and Stereochemical Revision of Coibamide A

Efficient Synthesis and Stereochemical Revision of Coibamide A

Guiyang Yao†‡, Zhengyin Pan†, Chunlei Wu†, Wei Wang†, Lijing Fang*†, and Wu Su*†
† Guangdong Key Laboratory of Nanomedicine, Institute of Biomedicine and Biotechnology, Shenzhen Institutes of Advanced Technology, Chinese Academy of Sciences, Shenzhen, Guangdong, 518055, P. R. China
‡ Departent of Pharmaceutical Engineering, School of Chemistry and Chemical Engineering, Southeast University, Nanjing, 211189, P. R. China

J. Am. Chem. Soc., 2015, 137 (42), pp 13488–13491
DOI: 10.1021/jacs.5b09286
Publication Date (Web): October 15, 2015
*lj.fang@siat.ac.cn, *wu.su@siat.ac.cn

Abstract

Coibamide A is a highly potent antiproLiferative cyclodepsipeptide originally isolated from a Panamanian marine cyanobacterium. Herein we report an efficient solid-phase strategy for assembly of highly N-methylated cyclodepsipeptides, which is invaluable in generating coibamide A derivatives for structure-activity relationship studies. As a consequence of our synthetic studies, two stereochemical assignments of coibamide A were revised and the total synthesis of this natural compound was achieved for the first time.

DOI: 10.1021/jacs.5b09286