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Easy Access to a Cyclic Key Intermediate for the Synthesis of Trisporic Acids and Related Compounds
Department of Organic Chemistry and Institute of Biotechnology, University of Granada, Avda Fuentenueva s/n, 18071 Granada, Spain
CIQSO–Center for Research in Sustainable Chemistry and Department of Chemical Engineering, Physical Chemistry and Organic Chemistry, University of Huelva, Avda 3 Marzo s/n, 21071 Huelva, Spain
University of Antioquia, Calle 70 N° 52-21, Medellín, Colombia
* Authors to whom correspondence should be addressed.
Received: 19 December 2013; in revised form: 22 January 2014 / Accepted: 23 January 2014 / Published: 3 February 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.
Keywords: trisporoids; apocarotenoid; domino reaction; stereoselective synthesis
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González-Delgado, J.A.; Escobar, G.; Arteaga, J.F.; Barrero, A.F. Easy Access to a Cyclic Key Intermediate for the Synthesis of Trisporic Acids and Related Compounds. Molecules 2014, 19, 1748-1762.
González-Delgado JA, Escobar G, Arteaga JF, Barrero AF. Easy Access to a Cyclic Key Intermediate for the Synthesis of Trisporic Acids and Related Compounds. Molecules. 2014; 19(2):1748-1762.
González-Delgado, José A.; Escobar, Gustavo; Arteaga, Jesús F.; Barrero, Alejandro F. 2014. "Easy Access to a Cyclic Key Intermediate for the Synthesis of Trisporic Acids and Related Compounds." Molecules 19, no. 2: 1748-1762.