Synthesis of (3<i>S</i>,4<i>S</i>)-Statine and a Related Compound, (3<i>S</i>,4<i>S</i>)-AHPPA, from <FONT SIZE="-2">D</FONT>-Glucosamine as a Chiral Pool

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  • Synthesis of(3S,4S)-Statine and a Related Compound,(3S,4S)-AHPPA,from D-Glucosamine as a Chiral Pool
  • Synthesis of 3S 4S-Statine and a Relate
  • Synthesis of (3<i>S</i>,4<i>S</i>)-Statine and a Related Compound, (3<i>S</i>,4<i>S</i>)-AHPPA, from <scp>d</scp>-Glucosamine as a Chiral Pool

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Abstract

Biologically important threo-β-hydroxy-γ-amino acids, (3S,4S)-statine ((3S,4S)-4-amino-3-hydroxy-6-methylheptanoic acid) (1) and (3S,4S)-AHPPA (3S,4S)-4-amino-3-hydroxy-5-phenylpentanoic acid) (2), were synthesized starting from D-glucosamine (3) as a chiral pool. Two routes for the transformation of D-glucosamine to key intermediates, which are applicable to the synthesis of threo-β-hydroxy-γ-amino acids, were investigated. The successful route involved C(6)-carbon degradation and elimination of the C(4)-hydroxy group of D-glucosamine in 8 steps and 30% overall yield to furnish (4R,5S)-2-oxo-5-vinyloxazolidine-4-carbaldehyde dimethyl acetal (17), which has been utilized as a versatile intermediate for synthesizing the target compounds.

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