Chemoenzymatic Synthesis of the Most Pleasant Stereoisomer of Jessemal

Chemoenzymatic Synthesis of the Most Pleasant Stereoisomer of Jessemal

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 dehydrogenas...

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Veröffentlicht in:Journal of organic chemistry 2022-05, Vol.87 (9), p.6499-6503
Hauptverfasser: Venturi, Silvia, Trajkovic, Milos, Colombo, Danilo, Brenna, Elisabetta, Fraaije, Marco W, Gatti, Francesco G, Macchi, Piero, Zamboni, Emilio
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Sprache:eng
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Acetates
Epoxy Compounds
Pyrans
Stereoisomerism
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container_end_page 6503
container_issue 9
container_start_page 6499
container_title Journal of organic chemistry
container_volume 87
creator Venturi, Silvia
Trajkovic, Milos
Colombo, Danilo
Brenna, Elisabetta
Fraaije, Marco W
Gatti, Francesco G
Macchi, Piero
Zamboni, Emilio
description 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.
doi_str_mv 10.1021/acs.joc.2c00427
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subjects Acetates
Epoxy Compounds
Pyrans
Stereoisomerism
title Chemoenzymatic Synthesis of the Most Pleasant Stereoisomer of Jessemal
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