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Beilstein-Institut, Beilstein Journal of Organic Chemistry, (8), p. 1344-1351, 2012

DOI: 10.3762/bjoc.8.154

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A macrolactonization approach to the total synthesis of the antimicrobial cyclic depsipeptide LI-F04a and diastereoisomeric analogues

Journal article published in 2012 by James R. Cochrane, Dong Hee Yoon, Christopher S. P. McErlean, Katrina A. Jolliffe ORCID
This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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Abstract

The cyclic peptide core of the antifungal and antibiotic cyclic depsipeptide LI-F04a was synthesised by using a modified Yamaguchi macrolactonization approach. Alternative methods of macrolactonization (e.g., Corey-Nicolaou) resulted in significant epimerization of the C-terminal amino acid during the cyclization reaction. The D-stereochemistry of the alanine residue in the naturally occurring cyclic peptide may be required for the antifungal activity of this natural product. © 2012 Cochrane et al; licensee Beilstein-Institut. License and terms: see end of document.