Chemoenzymatic preparation of functionalized bicyclo[3.2.1]octenone and practical utilization

Shinichiro Ito, Ayako Tosaka, Keisuke Hanada, Masatoshi Shibuya, Kunio Ogasawara, Yoshiharu Iwabuchi

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

A practical route for the synthesis of both enantiomers of a functionalized bicyclo[3.2.1]octenone, which is potentially useful as a versatile chiral building block, has been developed from 1,4-cyclohexanedione monoethylene acetal by employing proline-catalyzed diastereoselective intramolecular aldolization and lipase-mediated kinetic resolution as the key steps. The synthetic utility of the bicyclo[3.2.1]octenone has been demonstrated by the conversion into a chiral bicyclo[5.3.0]decane, which should serve as the key intermediate for the synthesis of the pseudoguaianolide class of antitumor sesquiterpenes.

Original languageEnglish
Pages (from-to)176-185
Number of pages10
JournalTetrahedron Asymmetry
Volume19
Issue number2
DOIs
Publication statusPublished - 2008 Feb 6

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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