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      Easy Access to a Cyclic Key Intermediate for the Synthesis of Trisporic Acids and Related Compounds

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          Abstract

          The synthesis of a cyclohexane skeleton possessing different oxygenated functional groups at C–3, C–8 and C–9, and a Δ 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.

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          Reagent-controlled transition-metal-catalyzed radical reactions.

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            Selective Generation of Free Radicals from Epoxides Using a Transition-Metal Radical. A Powerful New Tool for Organic Synthesis

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              Allylic oxidation of olefins by catalytic and stoichiometric selenium dioxide with tert-butyl hydroperoxide

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                Author and article information

                Journal
                Molecules
                Molecules
                molecules
                Molecules
                MDPI
                1420-3049
                03 February 2014
                February 2014
                : 19
                : 2
                : 1748-1762
                Affiliations
                [1 ]Department of Organic Chemistry and Institute of Biotechnology, University of Granada, Avda Fuentenueva s/n, 18071 Granada, Spain
                [2 ]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
                [3 ]University of Antioquia, Calle 70 N° 52-21, Medellín, Colombia
                Author notes
                [* ]Author to whom correspondence should be addressed; E-Mail: jesus.fernandez@ 123456diq.uhu.es (J.F.A.); afbarre@ 123456ugr.es (A.F.B.); Tel./Fax: +34-958-243-318.
                Article
                molecules-19-01748
                10.3390/molecules19021748
                6271007
                24496268
                2a622979-73bd-44d7-b619-c586c1dfd687
                © 2014 by the authors.

                Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license ( http://creativecommons.org/licenses/by/3.0/).

                History
                : 19 December 2013
                : 22 January 2014
                : 23 January 2014
                Categories
                Article

                trisporoids,apocarotenoid,domino reaction,stereoselective synthesis

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