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Synlett 1997; 1997(6): 707-709
DOI: 10.1055/s-1997-3270
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Preparation of a Promising Cyclobutanone Chiral Building Block: Its Stereochemistry and Utilization

Takahiko Taniguchi, Yasuo Goto, Kunio Ogasawara*
  • *Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-77, Japan, Fax +81-22-217-6845, E-mail konol@mail.cc.tohoku.ac.jp
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Publication History

Publication Date:
31 December 2000 (online)

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A cyclobutanone possessing a bicyclo[2.2.1]heptene framework {endo-tricyclo[4.2.1.02,5]non-7-en-3-one} has been prepared in both enantiomeric forms employing lipase-mediated kinetic resolution as the key step. To determine the absolute configuration, as well as to demonstrate the synthetic potential, both enantiomers of the cyclobutanone obtained have been transformed enantioconvergently into the key intermediate of the sequiterpene (+)-β-santalene and the iridoid monoterpene (-)-boschnialactone.

chiral building block - endo-tricyclo[4.2.1.02,5]non-7-en-3-one - iridoid monoterpene - lipase-mediated kinetic resolution - enantioconvergent synthesis

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