Lactones. 6. Microbial lactonization of gamma,delta-epoxy esters
Lactones. 6. Microbial lactonization of gamma,delta-epoxy esters
- Chirality: The Pharmacological, Biological, and Chemical Consequences of Molecular Asymmetry, 13(6), p.302-307, 2001 .
The ability of 19 microorganisms to perform the enantioselective lactonization of racemic gamma,delta-epoxy ester 3a and its 7-methyl homolog 3b was checked. It was found that Rhodotorula rubra preferentialy transformed both substrates to (-)-enantiomers of trans delta-hydroxy-gamma-lactones with ee 76 percent for 3a and 24 percent for 3b. The best efficiency (20-30 percent)and enantioselectivity (ee 60-100 percent)of formation of (-)-gamma-hydroxy-delta-lactones 6a and 6b was observed for lactonization by Botrytis cinerea and Fusarium semitectum, respectively.
TERPENOID LACTONES
BIOCATALYSTS
SHARPLESS EPOXIDATION
MICROORGANISMS
RHODOTORULA RUBRA
BOTRYTIS CINEREA
FUSARIUM SEMITECTUM
The ability of 19 microorganisms to perform the enantioselective lactonization of racemic gamma,delta-epoxy ester 3a and its 7-methyl homolog 3b was checked. It was found that Rhodotorula rubra preferentialy transformed both substrates to (-)-enantiomers of trans delta-hydroxy-gamma-lactones with ee 76 percent for 3a and 24 percent for 3b. The best efficiency (20-30 percent)and enantioselectivity (ee 60-100 percent)of formation of (-)-gamma-hydroxy-delta-lactones 6a and 6b was observed for lactonization by Botrytis cinerea and Fusarium semitectum, respectively.
TERPENOID LACTONES
BIOCATALYSTS
SHARPLESS EPOXIDATION
MICROORGANISMS
RHODOTORULA RUBRA
BOTRYTIS CINEREA
FUSARIUM SEMITECTUM