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Chemoenzymatic Synthesis of the Most Pleasant Stereoisomer of Jessemal
[Image: see text] 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 al...
| Autores principales: | , , , , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
American Chemical Society
2022
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| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9087343/ https://www.ncbi.nlm.nih.gov/pubmed/35442680 http://dx.doi.org/10.1021/acs.joc.2c00427 |
| _version_ | 1784704183525441536 |
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| author | Venturi, Silvia Trajkovic, Milos Colombo, Danilo Brenna, Elisabetta Fraaije, Marco W. Gatti, Francesco G. Macchi, Piero Zamboni, Emilio |
| author_facet | Venturi, Silvia Trajkovic, Milos Colombo, Danilo Brenna, Elisabetta Fraaije, Marco W. Gatti, Francesco G. Macchi, Piero Zamboni, Emilio |
| author_sort | Venturi, Silvia |
| collection | PubMed |
| description | [Image: see text] 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. |
| format | Online Article Text |
| id | pubmed-9087343 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2022 |
| publisher | American Chemical Society |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-90873432022-05-11 Chemoenzymatic Synthesis of the Most Pleasant Stereoisomer of Jessemal Venturi, Silvia Trajkovic, Milos Colombo, Danilo Brenna, Elisabetta Fraaije, Marco W. Gatti, Francesco G. Macchi, Piero Zamboni, Emilio J Org Chem [Image: see text] 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. American Chemical Society 2022-04-20 2022-05-06 /pmc/articles/PMC9087343/ /pubmed/35442680 http://dx.doi.org/10.1021/acs.joc.2c00427 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/). |
| spellingShingle | Venturi, Silvia Trajkovic, Milos Colombo, Danilo Brenna, Elisabetta Fraaije, Marco W. Gatti, Francesco G. Macchi, Piero Zamboni, Emilio Chemoenzymatic Synthesis of the Most Pleasant Stereoisomer of Jessemal |
| title | Chemoenzymatic Synthesis
of the Most Pleasant Stereoisomer
of Jessemal |
| title_full | Chemoenzymatic Synthesis
of the Most Pleasant Stereoisomer
of Jessemal |
| title_fullStr | Chemoenzymatic Synthesis
of the Most Pleasant Stereoisomer
of Jessemal |
| title_full_unstemmed | Chemoenzymatic Synthesis
of the Most Pleasant Stereoisomer
of Jessemal |
| title_short | Chemoenzymatic Synthesis
of the Most Pleasant Stereoisomer
of Jessemal |
| title_sort | chemoenzymatic synthesis
of the most pleasant stereoisomer
of jessemal |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9087343/ https://www.ncbi.nlm.nih.gov/pubmed/35442680 http://dx.doi.org/10.1021/acs.joc.2c00427 |
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