Enantiospecific Synthesis of (3<I>S</I>, 4<I>S</I>)-Statine and Its Analogue from D-Glucosamine as a Chiral Pool

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The C(6)-carbon degradation and elimination of C(4)-hydroxy group of D-glucosamine were achieved in 8-steps and 30% overall yield to furnish (4R, 5S)-5-vinyl-2-oxazolidinone-4-carbaldehyde dimethyl acetal, which was utilized as a key intermediate for enantiospecific synthesis of biologically important threo β-hydroxy-γ-amino acids, natural (3S, 4S)-statine and (3S, 4S)-AHPPA

Journal

  • Chemistry Letters

    Chemistry Letters 21 (12), 2265-2268, 1992

    The Chemical Society of Japan

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