Chemoenzymatic Synthesis of the Most Pleasant Stereoisomer of Jessemal

Silvia Venturi, Milos Trajkovic, Danilo Colombo, Elisabetta Brenna, Marco W Fraaije, Francesco G Gatti*, Piero Macchi, Emilio Zamboni

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

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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.

Original languageEnglish
Pages (from-to)6499-6503
Number of pages5
JournalThe Journal of Organic Chemistry
Volume87
Issue number9
Early online date20-Apr-2022
DOIs
Publication statusPublished - 6-May-2022

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