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Synlett 1996; 1996(4): 319-320
DOI: 10.1055/s-1996-5437
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An Expedient Route to (-)-cis-2-Oxabicyclo[3.3.0]oct-6-en-3-one via a meso-Asymmetrization

Tsutomu Sugahara, Kunio Ogasawara*
  • *Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-77, Japan, Fax +81-22-217-6845; E-mail c21799@cctu.cc.tohoku.ac.jp
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Publication Date:
31 December 2000 (online)

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The tricyclic meso-diol, obtained via contra-steric Diels-Alder reaction, has been transformed expediently into a versatile prostanoid building block, (-)-cis-2-oxabicyclo[3.3.0]oct-6-en-3-one, by lipase-mediated kinetic asymmetrization followed by concurrent three-fold thermal reaction.

meso-asymmetrization - lipase-mediated asymmetrization - prostanoid intermediate - pericyclic reaction - chiral ketodicyclopentadiene

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