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Synthesis 1993; 1993(1): 129-133
DOI: 10.1055/s-1993-25815
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New Routes to Isomerically Pure Cyclopentanes. Synthesis of (3S,4S)-3,4-Bis(benzoyloxymethyl)cyclopentan-1-ol using Palladium-Catalyzed [2 + 3] Cycloaddition

Marianne Janson* , Ingemar Kvarnström, Stefan C. T. Svensson, Björn Classon, Bertil Samuelsson
  • *Department of Chemistry, Linköping University, S-58183 Linköping, Sweden
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Publication Date:
17 September 2002 (online)

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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.