168416-67-9Relevant academic research and scientific papers
Synthesis of natural product precursors by Baeyer-Villiger oxidation with cyclohexanone monooxygenase from Acinetobacter
Schwarz-Linek, Ulrich,Kr?del, Andreas,Ludwig, Friedrich-Alexander,Schulze, Alexander,Rissom, Sebastian,Kragl, Udo,Tishkov, Vladimir I.,Vogel, Marina
, p. 947 - 951 (2001)
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.
The synthesis of (R)-(+)-lipoic acid using a monooxygenase-catalysed biotransformation as the key step
Adger, Brian,Bes, M. Teresa,Grogan, Gideon,McCague, Raymond,Pedragosa-Moreau, Sandrine,Roberts, Stanley M.,Villa, Raffaella,Wan, Peter W. H.,Willetts, Andrew J.
, p. 253 - 261 (2007/10/03)
2-(2-Acetoxyethyl)cyclohexanone (4) was converted into the lactone (-)-(5) regio- and enantioselectively using 2-oxo-Δ3-4,5,5-trimethylcyclopentenyl acetyl-CoA monooxygenase, an NADPH-dependent Baeyer-Villiger monooxygenase from camphor grown Pseudomonas putida NCIMB 10007. The lactone (-)-(5) was converted into (R)-(+)-lipoic acid in six steps. In contrast cyclopentanone monooxygenase, an NADPH-dependent Baeyer-Villiger monooxygenase from cyclopentanol-grown Pseudomonas sp. NCIMB 9872 selectively oxidized the (S)-enantiomer of the ketone (4) giving better access to optically enriched, naturally occurring lipoic acid.
Application of Enzymic Baeyer-Villiger Oxidations of 2-Substituted Cycloalkanones to the Total Synthesis of (R)-(+)-Lipoic Acid
Adger, Brian,Bes, M. Teresa,Grogan, Gideon,McCague, Ray,Pedragosa-Moreau, Sandrine,et al.
, p. 1563 - 1564 (2007/10/02)
Oxidation of ketones 1a-h using a monooxygenase from Pseudomonas putida NCIMB 10007 gave the lactones 2a-h in optically active form: lactone 2h was converted into (R)-(+)-lipoic acid 9.
