Synlett 1992; 1992(5): 388-390
DOI: 10.1055/s-1992-21354
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Enantioselective Syntheses of Conduramines from Benzene by Microbial Oxidation, Enzymatic Asymmetrization and Resolution in Organic Media

Carl R. Johnson* , Patrick A. Plé, Lin Su, Mary Jane Heeg, Joseph P. Adams
  • *Department of Chemistry, Wayne State University, Detroit, Michigan 48202, USA
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Publication History

Publication Date:
08 March 2002 (online)

The enzymatic asymmetrization of meso-2,3-O-isopropylideneconduritol A (2) using Pseudomonas cepacia lipase in isopropenyl acetate followed by a displacement with phthalimide in a Mitsunobu procedure led, after simple chemical transformations to (-)-conduramine C-1 [(1R,2S,3R,4R)-4-amino-5-cyclohexene-1,2,3-triol (9)] and (+)-conduramine C-1 (13). Palladium-catalyzed introduction of phthalimide gave derivatives 5 and 6 of conduramine E-1 and conduramine F-4, respectively. Enzymatic resolution of alcohol 16 gave protected forms 20 and 21 of the enantiomers of conduramine A-1.

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