Efficient Synthesis and Stereochemical Revision of Coibamide A
- 15 October 2015
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 137 (42), 13488-13491
- https://doi.org/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.Keywords
Funding Information
- Chinese Academy of Sciences
- National Natural Science Foundation of China (21402232, 21432003)
- Shenzhen Sciences and Technology Innovation Council (JCYJ20150316143416083, KQCX20130628112914285, KQCX2015033117354154)
This publication has 27 references indexed in Scilit:
- Total Synthesis and Biological Evaluation of the Antibiotic Lysocin E and Its Enantiomeric, Epimeric, and N‐Demethylated AnaloguesAngewandte Chemie-International Edition, 2014
- Cyclodepsipeptides: A Rich Source of Biologically Active Compounds for Drug ResearchMolecules, 2014
- Stellatolides, a New Cyclodepsipeptide Family from the Sponge Ecionemia acervus: Isolation, Solid-Phase Total Synthesis, and Full Structural Assignment of Stellatolide AJournal of the American Chemical Society, 2014
- The first total synthesis of the cyclodepsipeptide pipecolidepsin ANature Communications, 2013
- Coibamide A Induces mTOR-Independent Autophagy and Cell Death in Human Glioblastoma CellsPLOS ONE, 2013
- Challenges in the Syntheses of Peptidic Natural ProductsSynthesis, 2012
- Synthesis of N-methylated cyclic peptidesNature Protocols, 2012
- N-Methylation of Peptides: A New Perspective in Medicinal ChemistryAccounts of Chemical Research, 2008
- Coibamide A, a Potent Antiproliferative Cyclic Depsipeptide from the Panamanian Marine Cyanobacterium Leptolyngbya sp.Journal of the American Chemical Society, 2008
- The cyclization of peptides and depsipeptidesJournal of Peptide Science, 2003