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

…, DH Yoon, CSP McErlean, KA Jolliffe

Index: Cochrane, James R.; Yoon, Dong Hee; McErlean, Christopher S.P.; Jolliffe, Katrina A. Beilstein Journal of Organic Chemistry, 2012 , vol. 8, p. 1344 - 1351

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Citation Number: 8

Abstract

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 (eg, 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 ...