Easy Access to a Cyclic Key Intermediate for the Synthesis of Trisporic Acids and Related Compounds
MetadatosMostrar el registro completo del ítem
TrisporiodsApocarotenoidDomino reactionStereoselective synthesis
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]
PatrocinadorThis project was supported by the Spanish Ministry of Economy and Competitiveness (project CTQ2010-16818-BQ).
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.