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The Journal of organic chemistry

Enzymatic desymmetrization of a meso polyol corresponding to the C(19)-C(27) segment of rifamycin S.


PMID 10750492

Abstract

The stereoselective acylation of meso polyol 2 by vinyl acetate (solvent and acyl donor) in the presence of porcine pancreas lipase gave the corresponding monoester 5 in good yield (76%) and high enantiomeric purity (ee > 98%). The enzymatic reaction was also highly regioselective for a primary alcohol end group, and the two unprotected secondary alcohols were not involved. Compound 5 corresponds to the C(19)-C(27) fragment of rifamycin S.

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R0950000 Rifamycin S, European Pharmacopoeia (EP) Reference Standard
C37H45NO12