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Synlett 1992; 1992(3): 243-245
DOI: 10.1055/s-1992-21329
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Lipase-Catalyzed Enantiotoposelective Hydrolysis of meso-Compounds Derived from 2- Cyclohexene-1,4-Diol: Synthesis of (-)-Conduritol C, (-)-Conduritol E, (-)-Conduritol F and a Homochiral Derivative of Conduritol A

L. Dumortier* , P. Liu, S. Dobbelaere, J. Van der Eycken, M. Vandewalle
  • *University of Gent, Department of Organic Chemistry, Laboratory for Organic Synthesis, Krijgslaan, 281 (S. 4), B-9000 Gent, Belgium
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Publication Date:
08 March 2002 (online)

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The lipase-catalyzed enantiotoposelective hydrolysis of diacetate 2 leads to the 4-acetoxy-2-cyclohexen-1-ols (+)-3 or (-)-3 with good enantiomeric excess, while the dibutyrates 5 and 10 afforded alcohols (+)-6 and (+)-11 in >95% ee. The synthesis of (-)-conduritol C, (-)-conduritol E and (-)-conduritol F and a homochiral derivative of conduritol A from (+)-6 and (+)-11 is described.