Efficient Synthesis and Stereochemical Revision of Coibamide A

  • J Am Chem Soc. 2015 Oct 28;137(42):13488-91. doi: 10.1021/jacs.5b09286.
Guiyang Yao  1  2 ,  Zhengyin Pan  1 ,  Chunlei Wu  1 ,  Wei Wang  1 ,  Lijing Fang  1 ,  Wu Su  1
Affiliations
  • 1. 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.
  • 2. Departent of Pharmaceutical Engineering, School of Chemistry and Chemical Engineering, Southeast University , Nanjing, 211189, P. R. China.
PMID: 26469305 DOI: 10.1021/jacs.5b09286
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.

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