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Please use this identifier to cite or link to this item: http://hdl.handle.net/10481/32032

Title: Easy Access to a Cyclic Key Intermediate for the Synthesis of Trisporic Acids and Related Compounds
Authors: González-Delgado, José A.
Escobar, Gustavo
Arteaga, Jesús F.
Fernández Barrero, Alejandro
Issue Date: 2014
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.
Sponsorship: This project was supported by the Spanish Ministry of Economy and Competitiveness (project CTQ2010-16818-BQ).
Publisher: MDPI
Keywords: Trisporiods
Apocarotenoid
Domino reaction
Stereoselective synthesis
URI: http://hdl.handle.net/10481/32032
ISSN: 1420-3049
Rights : Creative Commons Attribution-NonCommercial-NoDerivs 3.0 License
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]
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