Total synthesis and structural revision of lucentamycin A

Sujeewa Ranatunga, Chih Hang Anthony Tang, Chih Chi Andrew Hu, Juan R. Del Valle

Research output: Contribution to journalArticle

14 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)9859-9864
Number of pages6
JournalJournal of Organic Chemistry
Volume77
Issue number21
DOIs
StatePublished - Nov 2 2012

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Total synthesis and structural revision of lucentamycin A'. Together they form a unique fingerprint.

Cite this