New Routes to Isomerically Pure Cyclopentanes. Synthesis of (3S,4S)-3,4-Bis(benzoyloxymethyl)cyclopentan-1-ol using Palladium-Catalyzed [2 + 3] Cycloaddition

Authors:
  • MJMarianne Janson
    Marianne Janson
  • IKIngemar Kvarnström
    Ingemar Kvarnström
  • SSStefan C. T. Svensson
    Stefan C. T. Svensson
  • BCBjörn Classon
    Björn Classon
  • BSBertil Samuelsson
    Bertil Samuelsson
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Abstract
Two different routes to the enantiomerically pure (3S,4S)-3,4-bis-(benzoyloxymethyl)cyclopentan-1-ol (6), a useful intermediate for the synthesis of a number of natural products, are described. Formation of the chiral five-membered ring was achieved using a palladium-catalyzed [2+3] cycloaddition between 2-(acetoxymethyl)-3-(trimethylsilyl)propene and optically active methyl (E)-3-O-benzyl-5,6-dideoxy-1, 2-O-isopropylidene-α-D-xylo-hept-5-enofuranuronate or ethyl (4R, Z)-4,5-(isopropylidenedioxy)pent-2-enoate.