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Synlett 1992; 1992(1): 51-52
DOI: 10.1055/s-1992-21262
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The Total Synthesis of (+)-Palitantin

X. Deruyttere* , L. Dumortier, 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:
18 September 2002 (online)

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An asymmetric synthesis of (+)-palitantin [1;(2R,3R,5S,6R)-5-(1,3-heptadienyl) -2,3-dihydroxy-6-hydroxymethyl-cyclohexanone] is described, starting from the homochiral alcohol (-)-3 [(1S,2S,3R) -2,3-isopropylidenedioxycyclohexanol], obtained via lipase-mediated resolution. Key steps include a regioselective dehydration and stereoselective cuprate addition.