First Stereocontrolled Synthesis of the (3S,5R,7R,10R,11R)-C1-C13 Fragment of Nystatin A(1)

Guy Solladié; Nicole Wilb; Claude Bauder; Carlo Bonini; Licia Viggiani; Lucia Chiummiento

doi:10.1021/jo990245y

First Stereocontrolled Synthesis of the (3S,5R,7R,10R,11R)-C1-C13 Fragment of Nystatin A(1)

J Org Chem. 1999 Jul 23;64(15):5447-5452. doi: 10.1021/jo990245y.

Authors

Guy Solladié¹, Nicole Wilb, Claude Bauder, Carlo Bonini, Licia Viggiani, Lucia Chiummiento

Affiliation

¹ Dipartimento di Chimica, Università degli Studi della Basilicata, Via N. Sauro 85, 85100 Potenza, Italy.

PMID: 11674606
DOI: 10.1021/jo990245y

Abstract

A convergent stereoselective synthesis of the (3S,5R,7R,10R,11R)-C1-C13 fragment of Nystatin A(1) is reported in this paper. This fragment contains an all-syn-1,3,5-triol subunit and a syn-1,2-diol moiety. The main features of the synthesis are the enzymatic desymmetrization of a meso diol to obtain an enantiomerically pure syn-4,6-dihydroxy-2-keto-phosphonate, chiral sulfoxide chemistry to prepare an alpha-(R)-hydroxyaldehyde and 2-trimethylsilyl thiazole reagent to synthesize a syn-alpha,beta-(R,S)-dihydroxy aldehyde.