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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

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Chemoenzymatic Synthesis of the Most Pleasant Stereoisomer of Jessemal.

Venturi Silvia S   Trajkovic Milos M   Colombo Danilo D   Brenna Elisabetta E   Fraaije Marco W MW   Gatti Francesco G FG   Macchi Piero P   Zamboni Emilio E  

The Journal of organic chemistry 20220420 9

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 rationa  ...[more]

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