Kinetic Resolution in Transannular Morita-Baylis-Hillman Reaction: An Approximation to the Synthesis of Sesquiterpenes from Guaiane Family
An approximation to the synthesis of several sesquiterpenes from the Guaiane family is described in which the core structure was obtained through a transannular Morita-Baylis-Hillman reaction performed under kinetic resolution. Several manipulations of the obtained MBH adduct have been carried out d...
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MDPI AG
2022-01-01
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| Online Access: | https://www.mdpi.com/2073-4344/12/1/67 |
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| author | Raquel Mato Rubén Manzano Efraím Reyes Liher Prieto Uxue Uria Luisa Carrillo Jose L. Vicario |
| author_facet | Raquel Mato Rubén Manzano Efraím Reyes Liher Prieto Uxue Uria Luisa Carrillo Jose L. Vicario |
| author_sort | Raquel Mato |
| collection | DOAJ |
| description | An approximation to the synthesis of several sesquiterpenes from the Guaiane family is described in which the core structure was obtained through a transannular Morita-Baylis-Hillman reaction performed under kinetic resolution. Several manipulations of the obtained MBH adduct have been carried out directed towards the total synthesis of γ-Gurjunene, to the formal synthesis of Clavukerin A, to the synthesis of a non-natural isomer of <i>isoguaiane</i> and to the synthesis of an advanced intermediate in the total synthesis of Palustrol. |
| first_indexed | 2024-03-10T01:45:41Z |
| format | Article |
| id | doaj.art-e47adb0d3408451faf39dcf3dd7376ed |
| institution | Directory Open Access Journal |
| issn | 2073-4344 |
| language | English |
| last_indexed | 2024-03-10T01:45:41Z |
| publishDate | 2022-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Catalysts |
| spelling | doaj.art-e47adb0d3408451faf39dcf3dd7376ed2023-11-23T13:16:34ZengMDPI AGCatalysts2073-43442022-01-011216710.3390/catal12010067Kinetic Resolution in Transannular Morita-Baylis-Hillman Reaction: An Approximation to the Synthesis of Sesquiterpenes from Guaiane FamilyRaquel Mato0Rubén Manzano1Efraím Reyes2Liher Prieto3Uxue Uria4Luisa Carrillo5Jose L. Vicario6Department of Organic and Inorganic Chemistry, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080 Bilbao, SpainDepartment of Organic and Inorganic Chemistry, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080 Bilbao, SpainDepartment of Organic and Inorganic Chemistry, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080 Bilbao, SpainDepartment of Organic and Inorganic Chemistry, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080 Bilbao, SpainDepartment of Organic and Inorganic Chemistry, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080 Bilbao, SpainDepartment of Organic and Inorganic Chemistry, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080 Bilbao, SpainDepartment of Organic and Inorganic Chemistry, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080 Bilbao, SpainAn approximation to the synthesis of several sesquiterpenes from the Guaiane family is described in which the core structure was obtained through a transannular Morita-Baylis-Hillman reaction performed under kinetic resolution. Several manipulations of the obtained MBH adduct have been carried out directed towards the total synthesis of γ-Gurjunene, to the formal synthesis of Clavukerin A, to the synthesis of a non-natural isomer of <i>isoguaiane</i> and to the synthesis of an advanced intermediate in the total synthesis of Palustrol.https://www.mdpi.com/2073-4344/12/1/67Morita-Baylis-Hillmantransannularkinetic resolutionsesquiterpenephosphinecatalysis |
| spellingShingle | Raquel Mato Rubén Manzano Efraím Reyes Liher Prieto Uxue Uria Luisa Carrillo Jose L. Vicario Kinetic Resolution in Transannular Morita-Baylis-Hillman Reaction: An Approximation to the Synthesis of Sesquiterpenes from Guaiane Family Catalysts Morita-Baylis-Hillman transannular kinetic resolution sesquiterpene phosphine catalysis |
| title | Kinetic Resolution in Transannular Morita-Baylis-Hillman Reaction: An Approximation to the Synthesis of Sesquiterpenes from Guaiane Family |
| title_full | Kinetic Resolution in Transannular Morita-Baylis-Hillman Reaction: An Approximation to the Synthesis of Sesquiterpenes from Guaiane Family |
| title_fullStr | Kinetic Resolution in Transannular Morita-Baylis-Hillman Reaction: An Approximation to the Synthesis of Sesquiterpenes from Guaiane Family |
| title_full_unstemmed | Kinetic Resolution in Transannular Morita-Baylis-Hillman Reaction: An Approximation to the Synthesis of Sesquiterpenes from Guaiane Family |
| title_short | Kinetic Resolution in Transannular Morita-Baylis-Hillman Reaction: An Approximation to the Synthesis of Sesquiterpenes from Guaiane Family |
| title_sort | kinetic resolution in transannular morita baylis hillman reaction an approximation to the synthesis of sesquiterpenes from guaiane family |
| topic | Morita-Baylis-Hillman transannular kinetic resolution sesquiterpene phosphine catalysis |
| url | https://www.mdpi.com/2073-4344/12/1/67 |
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