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

Hiromi Nakashima; Masayuki Sato; Takahiko Taniguchi; Kunio Ogasawara

doi:10.1055/s-1999-2956

Synlett 1999; 1999(11): 1754-1756
DOI: 10.1055/s-1999-2956

letter

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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

Hiromi Nakashima^* , Masayuki Sato, Takahiko Taniguchi, Kunio Ogasawara

^*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan; Fax +81-22-2 17-68 45; E-mail: konol@mail.cc.tohoku.ac.jp

Abstract

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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.

chiral building block - prostaglandin building block - kinetic resolution - lipase-mediated kinetic transesterification - enantioconvergent synthesis

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