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Synthesis 1995; 1995(10): 1237-1239
DOI: 10.1055/s-1995-4092
short paper
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An Expedient Route to Optically Pure 3-endo-Hydroxydicyclopentadiene

Keigo Tanaka, 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 Date:
31 December 2000 (online)

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Optically pure 3-endo-hydroxydicyclopentadiene has been prepared expediently in both enantiomeric forms via lipase-mediated kinetic resolution. Manganese dioxide transforms the optically active 3-endo-alcohol into the highly versatile chiral building block 3-oxo-dicyclopentadiene without loss of optical purity.

lipase-mediated kinetic resolution - 3-endo-hydroxydicyclopentadiene - kinetic deacetylation - kinetic methanolysis - cyclopentadienone synthon