Easy Access to a Cyclic Key Intermediate for the Synthesis of Trisporic Acids and Related Compounds
| Autor: | Jesús F. Arteaga, José A. González-Delgado, Gustavo Escobar, Alejandro F. Barrero |
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| Jazyk: | angličtina |
| Rok vydání: | 2014 |
| Předmět: |
Cyclohexane
Stereochemistry Trisporoids Pharmaceutical Science Epoxide trisporoids Radical cyclization Article Catalysis Analytical Chemistry lcsh:QD241-441 chemistry.chemical_compound Cascade reaction lcsh:Organic chemistry domino reaction Cyclohexanes Drug Discovery Moiety Physical and Theoretical Chemistry stereoselective synthesis Trisporiods Molecular Structure Organic Chemistry Domino reaction Stereoselective synthesis Regioselectivity Stereoisomerism Carbon Homolysis chemistry Chemistry (miscellaneous) Cyclization apocarotenoid Apocarotenoid Fatty Acids Unsaturated Molecular Medicine Epoxy Compounds Derivative (chemistry) |
| Zdroj: | Molecules Molecules, Vol 19, Iss 2, Pp 1748-1762 (2014) Arias Montano. Repositorio Institucional de la Universidad de Huelva instname Volume 19 Issue 2 Pages 1748-1762 Digibug. Repositorio Institucional de la Universidad de Granada |
| ISSN: | 1420-3049 |
| Popis: | The synthesis of a cyclohexane skeleton possessing different oxygenated functional groups at C–3, C–8 and C–9, and a 1,6-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. This project was supported by the Spanish Ministry of Economy and Competitiveness (project CTQ2010-16818-BQ). |
| Databáze: | OpenAIRE |
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