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Synlett 2001; 2001(10): 1650-1652
DOI: 10.1055/s-2001-17487
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Lipase-Catalyzed Asymmetrization of Diacetate of Meso-2-(2-Propynyl)cyclohexane-1,2,3-triol toward the Total Synthesis of Aquayamycin

Takashi Matsumoto* , Tadayoshi Konegawa, Hiroki Yamaguchi, Takeshi Nakamura, Takeshi Sugai, Keisuke Suzuki
  • *Department of Chemistry, Tokyo Institute of Technology and CREST, Japan Science and Technology Corporation (JST), Tokyo 152-8551, Japan; Fax + 81(3)57 34 35 31
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Publication Date:
27 September 2001 (online)

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The diacetate of meso-2-(2-propynyl)cyclohexane-1,2,3-triol was efficiently asymmetrized by hydrolysis with Candida antarctica lipase to give the corresponding mono-acetate in enantiomerically pure form, which was used as the starting material for the total synthesis of aquayamycin. Application of the protocol to the related cyclohexanetriols is also described.

asymmetrization - hydrolysis - enzyme - meso compound - total synthesis

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