title: Universal access to megastigmanes through controlled cyclisation towards highly substituted cyclohexenes.
abstract: We report the selective formation of cyclohexenes with a tetrasubstituted double bond, the structural key element of megastigmanes. For this purpose the ZrCl4-mediated epoxide ring opening of epoxy-geranylacetone was employed. This approach provides a universal entry to the preparation of the members of the megastigmane family, which was exemplified in the asymmetric synthesis of tectoionol B.
authors.affiliation: CIQSO - Centre for Research in Sustainable Chemistry and Department of Chemistry, University of Huelva, Campus de El Carmen s/n, 21071 Huelva, Spain. jesus.fernandez@diq.uhu.es.
authors.forename: José A
authors.initials: JA
authors.lastname: González-Delgado
authors.affiliation: CIQSO - Centre for Research in Sustainable Chemistry and Department of Chemistry, University of Huelva, Campus de El Carmen s/n, 21071 Huelva, Spain. jesus.fernandez@diq.uhu.es.
authors.forename: Miguel A
authors.initials: MA
authors.lastname: Romero
authors.affiliation: CIQSO - Centre for Research in Sustainable Chemistry and Department of Chemistry, University of Huelva, Campus de El Carmen s/n, 21071 Huelva, Spain. jesus.fernandez@diq.uhu.es.
authors.forename: Uwe
authors.initials: U
authors.lastname: Pischel
authors.affiliation: CIQSO - Centre for Research in Sustainable Chemistry and Department of Chemistry, University of Huelva, Campus de El Carmen s/n, 21071 Huelva, Spain. jesus.fernandez@diq.uhu.es.
authors.forename: Jesús F
authors.initials: JF
authors.lastname: Arteaga
mesh_terms: D003500:Cyclization; D003512:Cyclohexanones / Q000737:chemistry*; D053138:Cyclohexenes / Q000138:chemical synthesis* / Q000737:chemistry; D005960:Glucosides / Q000737:chemistry*; D008968:Molecular Conformation; D045792:Norisoprenoids / Q000737:chemistry*
chemical_list: D003512:Cyclohexanones; D053138:Cyclohexenes; D005960:Glucosides; D045792:Norisoprenoids; C413264:megastigmane