Chemoenzymatic Synthesis of the Most Pleasant Stereoisomer of Jessemal.

ABSTRACT: We describe the asymmetric synthesis of the most pleasant enantiomer of Jessemal fragrance. The key steps are (i) the one-pot reduction of an α-chloro-tetrasubstituted cyclohexenone to give the chlorohydrin, catalyzed by two stereoselective redox enzymes (an ene-reductase and an alcohol dehydrogenase); (ii) the regioselective epoxide ring-opening with organocuprate or organolithium nucleophiles. Density functional theory calculations together with the Curtin-Hammett principle allowed the rationalization of the regioselectivity.

SUBMITTER: Venturi S 

PROVIDER: S-EPMC9087343 | biostudies-literature | 2022 May

REPOSITORIES: biostudies-literature