RT Journal Article
T1 Easy Access to a Cyclic Key Intermediate for the Synthesis of Trisporic Acids and Related Compounds
A1 González Delgado, José Ángel
A1 Escobar, Gustavo
A1 Fernández Arteaga, Jesús
A1 Barrero, Alejandro F.
AB The synthesis of a cyclohexane skeleton possessing different oxygenatedfunctional groups at C–3, C–8 and C–9, and a 1,6-double bond has been accomplished in10 steps with an overall 17% yield. This compound is a key intermediate for access to awide range of compounds of the bioactive trisporoid family. The synthetic sequenceconsists of the preparation of a properly functionalized epoxygeraniol derivative, and itssubsequent stereoselective cyclization mediated by Ti(III). This last step implies a dominoprocess that starts with a homolytic epoxide opening followed by a radical cyclization andregioselective elimination. This concerted process gives access to the cyclohexane moietywith stereochemical control of five of its six carbon atoms.
PB MDPI
YR 2014
FD 2014
LK http://hdl.handle.net/10272/13564
UL http://hdl.handle.net/10272/13564
LA eng
NO González Delgado, J.A., Escobar, G., Fernández Arteaga, J. Barrero, A.: "Easy Access to a Cyclic Key Intermediate for the Synthesis of Trisporic Acids and Related Compounds". Molecules. Vol. 19, págs. 1748-1762, (2014). DOI: 10.3390/molecules19021748
NO This project was supported by the Spanish Ministry of Economy and Competitiveness (project CTQ2010-16818-BQ).
DS Repositorio Institucional de la Universidad de Huelva
RD 31 may 2026