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Synthesis 1995; 1995(4): 444-448
DOI: 10.1055/s-1995-3930
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Resolution and Utilization of Ethyl 5-Hydroxycyclopent-1-enecarboxylate: Enantioselective Synthesis of (+)-Mitsugashiwalactone and (-)-Dolichodial

Takahiro Yamane, Michiyasu Takahashi, Kunio Ogasawara*
  • *Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-77, Japan, Fax +81(22)2681541
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Publication Date:
31 December 2000 (online)

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Optically pure ethyl 5-hydroxycyclopent-1-enecarboxylate has been obtained with its acetate in both enantiomeric forms in excellent optical yields from racemic ethyl 5-hydroxycyclopent-1-enecarboxylate by lipase-mediated kinetic resolution. The optically pure (R)-enantiomer thus obtained has been transformed into two naturally occurring iridoid monoterpenes, (+)-mitsugashiwalactone and (-)-dolichodial.

lipase-mediated kinetic resolution - enantiocomplementary resolution - enantiocontrolled synthesis - (+)-mitsugashiwalactone - (-)-dolichodial