Synthesis of natural product precursors by Baeyer-Villiger oxidation with cyclohexanone monooxygenase from Acinetobacter

Ulrich Schwarz-Linek, A Krodel, FA Ludwig, A Schulze, S Rissom, U Kragl, VI Tishkov, M Vogel

Research output: Contribution to journalArticlepeer-review

45 Citations (Scopus)

Abstract

The Baeyer-Villiger oxidation of the 2-substituted ketones 1 and 3 with the coupled system cyclohexanone monooxygenase from Acinetobacter NCIMB 9871 / formate dehydrogenase from Pseudomonas sp. 101 provides the lactones (R)-2 and (R)-4 with high enantiomeric excess which are precursors in the synthesis of lipoic acid. The symmetrically trisubstituted ketone 5 was oxidised to the lactones 6a and 6b in a ratio of approx. 3:1. The absolute configuration of 6a and 6b was determined by hydrolysis of the racemic lactone with PLE yielding the hydroxycarboxylic acid (-)-7 with known absolute configuration.

Original languageEnglish
Pages (from-to)947-951
Number of pages5
JournalSynthesis
Issue number6
DOIs
Publication statusPublished - May 2001

Keywords

  • oxidation
  • enzymes
  • kinetic resolution
  • hydrolysis
  • natural products
  • FORMATE DEHYDROGENASE
  • AGGREGATION PHEROMONE
  • (R)-(+)-LIPOIC ACID
  • LARDOGLYPHUS-KONOI
  • EPSILON-LACTONES
  • ACARID MITE
  • OXYGENASE
  • RESOLUTION
  • LARDOLURE

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