Organic Synthesis with Enzymes. 3.1 TBADH-Catalyzed Reduction of Chloro Ketones. Total Synthesis of (+)-(S,S)-(cis-6-Methyltetrahydropyran-2-yl)acetic Acid: A Civet Constituent

Ehud Keinan, Kamal K. Seth, Raphael Lamed

Research output: Contribution to journalArticle

122 Scopus citations

Abstract

Highly enantioselective reduction of aliphatic chloro ketones catalyzed by Thermoanaerobium brockii alcohol dehydrogenase (TBADH) afforded the corresponding S chloro alcohols, which are new and useful chiral bifunctional building blocks. The synthetic potential of these compounds was illustrated by syntheses of several optically pure cyclic ethers. In particular, (S)-(+)-5-chloropentan-2-ol was used for the total synthesis of (+)-(S,S)-(cis-6-methyltetrahydropyran-2-yl) acetic acid, a natural constituent of the perfume material civet. Two of the key steps in the synthesis involve organopalladium chemistry: a Pd(0)-catalyzed intramolecular allylic etherification followed by a Pd(II)-catalyzed Wacker oxidation of the disubstituted olefin.

Original languageEnglish (US)
Pages (from-to)3474-3480
Number of pages7
JournalJournal of the American Chemical Society
Volume108
Issue number12
DOIs
StatePublished - Jan 1 1986

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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