Lipase-mediated Resolution of cis-4-Cumyloxy-2-cyclopenten-1-ol and its Utilization for Enantioconvergent Preparation of (-)-Oxabicyclo[3.3.0]-oct-6-en-3-one

Authors:
  • HNHiromi Nakashima
    Hiromi Nakashima
  • MSMasayuki Sato
    Masayuki Sato
  • TTTakahiko Taniguchi
    Takahiko Taniguchi
  • KOKunio Ogasawara
    Kunio Ogasawara
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Abstract
Convenient preparation of both enantiomers of cis-4-cumyloxy-2-cyclopenten-1-ol from cyclopentadiene employing a lipase-mediated resolution was first established. An efficient enantioconvergent transformation of both enantiomeric products affording (-)-oxabicyclo[3.3.0]oct-6-en-3-one, an important building block of prostaglandin synthesis, was next established.