Lactones. 6. Microbial lactonization of gamma,delta-epoxy esters

Tipo de material: Texto

TextoSeries ; Chirality: The Pharmacological, Biological, and Chemical Consequences of Molecular Asymmetry, 13(6), p.302-307, 2001Trabajos contenidos:

Olejniczak, T
Gawronski, J
Wawrzenczyk, C

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Resumen: 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.

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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.

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