First Stereocontrolled Synthesis of the (3S,5R,7R,10R,11R)-C1-C13 Fragment of Nystatin A(1).
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.
Solladié
Guy
G
Dipartimento di Chimica, Università degli Studi della Basilicata, Via N. Sauro 85, 85100 Potenza, Italy.
Wilb
Nicole
N
Bauder
Claude
C
Bonini
Carlo
C
Viggiani
Licia
L
Chiummiento
Lucia
L