Total Synthesis and Structural Revision of Lucentamycin A

Lucentamycin A is a marine-derived peptide natural product harboring a unique 4-ethylidene-3-methylproline (Emp) subunit. The proposed structure of lucentamycin A and the core Emp residue have recently been called into question through synthesis. Here, we report the first total synthesis of lucentam...

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Bibliographic Details
Published in:Journal of organic chemistry 2012-11, Vol.77 (21), p.9859-9864
Main Authors: Ranatunga, Sujeewa, Tang, Chih-Hang Anthony, Hu, Chih-Chi Andrew, Del Valle, Juan R
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Chemistry
Exact sciences and technology
Molecular Structure
Oligopeptides - chemical synthesis
Oligopeptides - chemistry
Organic chemistry
Peptides
Preparations and properties
Proline - analogs & derivatives
Proline - chemistry
Stereoisomerism
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Summary:Lucentamycin A is a marine-derived peptide natural product harboring a unique 4-ethylidene-3-methylproline (Emp) subunit. The proposed structure of lucentamycin A and the core Emp residue have recently been called into question through synthesis. Here, we report the first total synthesis of lucentamycin A, which confirms that the ethylidene substituent in Emp bears an E geometry, in contrast to the originally assigned Z configuration. Synthesis of the desired (E)-Emp subunit required the implementation of a novel strategy starting from Garner’s aldehyde.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo301723y