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Synlett 1999; 1999(S1): 893-896
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Site-Selective Epimerization of a Fungal Cyclodepsipeptide via a 5-Aminooxazole Intermediate
31 December 1999 (online)
The epimerization of the cyclic depsiheptapeptide 1 at a single amino acid (Leu) was achieved in four steps. After regio-selective thionation of 1 at one of its six amide-bonds, subsequent S-benzylation of the thioamide 2 led to the thioimidate 3, which was converted to the peptide-bridged 5-aminooxazole 5 by an unusual mercury promoted intramolecular cyclization. Re-opening of the oxazole ring by acid hydrolysis regenerated the parent cyclopeptolide framework 6, but preferentially with inverted configuration at leucine.
natural products - cyclodepsipeptide - epimerization - 5-aminooxazole