Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 21, Pages 9859-9864Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo301723y
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Funding
- Bankhead-Coley Biomedical Research Program, Florida Department of Health [1BN03]
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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 Gamer's aldehyde.
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