Lactones. 6. Microbial lactonization of gamma,delta-epoxy esters.
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% for 3a and 24% for 3b. The best efficiency (20-30%) and enantioselectivity (ee 60-100%) of formation of (-)-gamma-hydroxy-delta-lactones 6a and 6b was observed for lactonization by Botrytis cinerea and Fusarium semitectum, respectively.
Olejniczak
T
T
Department of Chemistry, Agricultural University, Wroclaw, Poland.
Gawroński
J
J
Wawrzeńczyk
C
C
D001711:Biotransformation; D004852:Epoxy Compounds / Q000737:chemistry / Q000378:metabolism*; D004952:Esters; D005658:Fungi / Q000378:metabolism*; D007783:Lactones / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy
D004852:Epoxy Compounds; D004952:Esters; D007783:Lactones