Baker's Yeast Reduction of N-Protected Methyl 4-Amino-3-oxobutanoates and 3-oxopentanoates

Shohei Hashiguchi; Akira Kawada; Hideaki Natsugari

doi:10.1055/s-1992-26123

Synthesis 1992; 1992(4): 403-408
DOI: 10.1055/s-1992-26123

paper

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Baker's Yeast Reduction of N-Protected Methyl 4-Amino-3-oxobutanoates and 3-oxopentanoates

Shohei Hashiguchi^* , Akira Kawada, Hideaki Natsugari

^*Chemistry Research Laboratories, Research and Development Division, Takeda Chemical Industries, Ltd., Yodogawa-ku, Osaka 532, Japan

Abstract

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Baker's yeast reduction of N-tert-butoxycarbonyl (Boc) or N-benzyloxycarbonyl(Cbz) protected methyl 4-amino-3-oxopentanoates 4b-e and 4-amino-3-oxobutanoates 7a,b stereoselectively afforded the erythro-hydroxy esters 5b-e and (R)-hydroxy esters 8a, b, respectively. The resulting N-protected methyl (R) -4-amino-3-hydroxybutanoate (8) was converted into the biologically active substances, sperabillin C 1c and (R)-GABOB [(R)4-amino-3-hydroxybutanoic acid. 2].

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