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Total synthesis and structural revision of lucentamycin A.

ABSTRACT: 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.

SUBMITTER: Ranatunga S

PROVIDER: S-EPMC5525334 | biostudies-literature | 2012 Nov

REPOSITORIES: biostudies-literature

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Total synthesis and structural revision of lucentamycin A.

Ranatunga Sujeewa S Tang Chih-Hang Anthony CH Hu Chih-Chi Andrew CC Del Valle Juan R JR

The Journal of organic chemistry 20121016 21

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 impleme ...[more]

PMID: 23039096

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