The enantioselective synthesis of C₁₈-sphingosines

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1995

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Virginia Tech

Abstract

Biocatalytic conversion of chlorobenzene to the corresponding homochiral cyclohexadiene cis-diol (113) allows, through careful symmetry-based planning, the stereodivergent synthesis of all sphingosine stereoisomers. This was achieved via the selective preparation of the appropriate diastereomer of azido alcohol (118), were C-4 and C-5 correspond to C-3 and C-2 of the sphingosine skeleton, respectively (Scheme 1).

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