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Synthesis 1996; 1996(9): 1101-1108
DOI: 10.1055/s-1996-4342
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A New Chiral Route to Optically Pure 3-Oxodicyclopentadiene: A Versatile Chiral Cyclopentadienone Synthon, via Contra-Steric Diels-Alder Reaction

Tsutomu Sugahara, Yukari Kuroyanagi, Kunio Ogasawara*
  • *Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-77, Japan, Fax +81(22)2176845; E-mail c21799@cctu.cc.tohoku.ac.jp
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Publication History

Publication Date:
31 December 2000 (online)

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Optically pure oxodicyclopentadiene (KDP) has been prepared in both enantiomeric forms from racemic 4-tert-butoxycyclopent-2-en-1-one in three ways starting from 4-tert-butoxycyclopent-2-en-1-one involving contra-steric Diels-Alder reaction and lipase-mediated enantiospecific kinetic transesterification as key steps.

contra-steric Diels-Alder reaction - chiral synthon - lipase-mediated kinetic transesterification - meso trick - symmetrization - chiral cyclopentadienone synthon - oxodicyclopentadiene