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Synthesis 1991; 1991(6): 487-490
DOI: 10.1055/s-1991-26502
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Preparative Bioorganic Chemistry; XIV.1 Preparation of (2S,3S)-1-Phenylthio-2,3-pentanediol and (2S,3S)-1-Phenylsulfonyl-2,3-pentanediol by Yeast Reduction of the Corresponding Diketones, and Conversion of the Former to (+)-endo-Brevicomin

Kenji Mori* , Masaharu Ishikura, Young-Bae Seu
  • *Department of Agricultural Chemistry, The University of Tokyo, Yayoi 1-1-1, Bunyo-ku, Tokyo 113, Japan
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Publication Date:
29 April 2002 (online)

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(2S,3S)-1-Phenylthio-2,3-pentanediol (2) and 2S,3S)-1-phenylsulfonyl-2,3-pentanediol (16) were prepared by reducing the corresponding diketones, 6 and 15, with baker's yeast. Conversion of 2 to (3S,4R)-8-nonene-3,4-diol (13), the key intermediate for the synthesis of (+)-endo-brevicomin [endo -7-ethyl-5-methyl-6,8-dioxabicyclo[3.2.1]octane, (1R,5S,7S) -1], is also described.