Enzymatic preparation of an optically active precursor of the CC-1065/duocarmycin pharmacophore

Acetylation of 2-[4-(benzyloxy)-2-nitrophenyl]propane-1,3-diol with vinyl acetate in the presence of porcine pancreatic lipase gave the (R)-mono-acetate (ee = 92%). The (S)-mono-acetate was obtained via acetylation of the diol followed by transesterification in ethanol in the presence of the same en...

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Bibliographic Details
Published inChemistry letters no. 1; pp. 11 - 12
Main Authors Chenevert, R, Courchesne, G
Format Journal Article
LanguageEnglish
Published TOKYO Chemical Soc Japan 01.01.1997
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
1,2,7,7A-TETRAHYDROCYCLOPROP<1,2-C>INDOL-4-ONE
STREPTOMYCES
CC-1065
DUOCARMYCIN-A
BIOLOGICAL-ACTIVITY
SUBUNIT
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Summary:Acetylation of 2-[4-(benzyloxy)-2-nitrophenyl]propane-1,3-diol with vinyl acetate in the presence of porcine pancreatic lipase gave the (R)-mono-acetate (ee = 92%). The (S)-mono-acetate was obtained via acetylation of the diol followed by transesterification in ethanol in the presence of the same enzyme. Incorporation of these optically active mono-acetates into the established synthetic routes provided access to both enantiomers of the common pharmacophore of CC-1065/duocarmycin.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.1997.11