dc.contributor.author | González-Delgado, José A. | |
dc.contributor.author | Escobar, Gustavo | |
dc.contributor.author | Arteaga, Jesús F. | |
dc.contributor.author | Fernández Barrero, Alejandro | |
dc.date.accessioned | 2014-05-29T13:18:12Z | |
dc.date.available | 2014-05-29T13:18:12Z | |
dc.date.issued | 2014 | |
dc.identifier.citation | González-Delgado, J.A.; et al. Easy Access to a Cyclic Key Intermediate for the Synthesis of Trisporic Acids and Related Compounds. Molecules, 19(2): 1748-1762 (2014). [http://hdl.handle.net/10481/32032] | es_ES |
dc.identifier.issn | 1420-3049 | |
dc.identifier.uri | http://hdl.handle.net/10481/32032 | |
dc.description.abstract | The synthesis of a cyclohexane skeleton possessing different oxygenated functional groups at C–3, C–8 and C–9, and a D1,6-double bond has been accomplished in 10 steps with an overall 17% yield. This compound is a key intermediate for access to a wide range of compounds of the bioactive trisporoid family. The synthetic sequence consists of the preparation of a properly functionalized epoxygeraniol derivative, and its subsequent stereoselective cyclization mediated by Ti(III). This last step implies a domino process that starts with a homolytic epoxide opening followed by a radical cyclization and regioselective elimination. This concerted process gives access to the cyclohexane moiety with stereochemical control of five of its six carbon atoms. | es_ES |
dc.description.sponsorship | This project was supported by the Spanish Ministry of Economy and Competitiveness (project
CTQ2010-16818-BQ). | es_ES |
dc.language.iso | eng | es_ES |
dc.publisher | MDPI | es_ES |
dc.rights | Creative Commons Attribution-NonCommercial-NoDerivs 3.0 License | es_ES |
dc.rights.uri | http://creativecommons.org/licenses/by-nc-nd/3.0/ | es_ES |
dc.subject | Trisporiods | es_ES |
dc.subject | Apocarotenoid | es_ES |
dc.subject | Domino reaction | es_ES |
dc.subject | Stereoselective synthesis | es_ES |
dc.title | Easy Access to a Cyclic Key Intermediate for the Synthesis of Trisporic Acids and Related Compounds | es_ES |
dc.type | journal article | es_ES |
dc.rights.accessRights | open access | es_ES |
dc.identifier.doi | 10.3390/molecules19021748 | |