Stereoselective formation of metabolites from 2-methyl-2-hepten-6-one by Botrytis cinerea

Add time:08/04/2019    Source:sciencedirect.com

Controlled conversion of 2-methyl-2-hepten-6-one (1) by Botrytis cinerea resulted in the formation of (S)-(+)-2-methyl-2-hepten-6-ol (sulcatol) (2) of 90% ee. In addition, (2R, 5R)- (3a), (2S,5S)- (3a′), (2R,5S)- (3b) and (2S,5R)-2-(1-hydroxy-1-methylethyl )-5-methyltetrahydrofuran (3b′), (3s, 6R)- (4a), (3R,6S)- (4a′), (3R,6R)- (4b) and (3S,6S)-tetrahydro-2,2,6-trimethyl-2H-pyran-3-ol (4b′) as well as the diastereomeric dihydro-3-hydroxy-5-methyl-5-(2′-methyl-pent-2-en-5′-yl)-2(3H)-furanones (5a/b) were found as biotransformations products of 1. Chiral analysis carried out by on-line multidimensional gas chromatography-mass spectrometry (MDGC-MS) revealed the following ee values: 46 % (3a); 80 % (3b); 56 % (4a); and 60 % (4b′). As confirmed by nOe experiments, 5a/b were formed in a ratio of 6:1.

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