Thermostable enzymes in organic synthesis, 4. Tbadh-catalyzed preparation of bifunctional chirons. Total synthesis of s-(+z-tetradec-5-en-13-olide

Ehud Keinan*, Kamal K. Seth, Raphael Lamed, Rodolfo Ghirlando, Surendra P. Singh

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

31 Scopus citations

Abstract

Highly enantioselective reduction of various methyl- and ethylketones bearing different functional groups, such as double and triple carbon-carbon bonds, methyl ester, cyano, ethyl ether, phenyl and chloride, employing Thermoanaerobium brockii alcohol dehydrogenase (TBADH) as a catalyst, affords the corresponding optically active, secondary alcohols. As expected on the basis of our previous studies with monofunctional ketones, reduction of most of the substrates yields, uniformly, alcohols with an S configuration, arising from highly selective hydride attack at the re face of the carbonyl. However, with the smaller-sized ketones, there is a clear reversal in stereoselectivity. The synthetic usefulness of these chiral building blocks has been demonstrated by the total synthesis of (S)-(+Z-tetradec-5-en-13-olide, one of several synergistic aggregation pheromones produced by male flat grain beetles, Cryptolestes pusillus (Schonherr). The pheromone was prepared from (S)-(+methyl-8-hydroxynonanoate with optical purity greater than 99% in a six-step synthesis.

Original languageEnglish (US)
Pages (from-to)57-71
Number of pages15
JournalBiocatalysis and Biotransformation
Volume3
Issue number1-2
DOIs
StatePublished - 1990

Keywords

  • Alcohol dehydrogenase
  • Enantioselective reduction
  • Pheromone synthesis
  • Thermoanaerobium brockü

ASJC Scopus subject areas

  • Biotechnology
  • Catalysis
  • Biochemistry

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