First stereocontrolled synthesis of the (3S,5R,7R,10R,11R)-C1-C13 fragmentof nystatin A(1)

Authors
Solladie, G Wilb, N Bauder, C Bonini, C Viggiani, L Chiummiento, L
Citation
G. Solladie et al., First stereocontrolled synthesis of the (3S,5R,7R,10R,11R)-C1-C13 fragmentof nystatin A(1), J ORG CHEM, 64(15), 1999, pp. 5447-5452
Citations number
25
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
64
Issue
15
Year of publication
1999
Pages
5447 - 5452
Database
ISI
SICI code
0022-3263(19990723)64:15<5447:FSSOT(>2.0.ZU;2-X
Abstract
A convergent stereoselective synthesis of the (3S,5R,7R,10R,11R)-C1-C13 fra gment of Nystatin Al is reported in this paper. This fragment contains an a ll-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 a n enantiomerically pure syn-4,6-dihydroxy-2-keto-phosphonate, chiral sulfox ide chemistry to prepare an alpha-(R)-hydroxyaldehyde and 2-trimethylsilyl thiazole reagent to synthesize a synthesize a syn-alpha,beta-(R,S)-dihydrox y aldehyde.