Convenient route to enantiopure aryl cyclopentanes via Diels-Alder reaction of asymmetric dienes. Total synthesis of (+)-herbertene and (+)-cuparene

Nayek, A. , Drew, M.G.B. and Ghosh, S. (2003) Convenient route to enantiopure aryl cyclopentanes via Diels-Alder reaction of asymmetric dienes. Total synthesis of (+)-herbertene and (+)-cuparene. Tetrahedron, 59 (28). pp. 5175-5181. ISSN 0040-4020 doi: 10.1016/S0040-4020(03)00807-X

Abstract/Summary

A general route for the synthesis of highly substituted aryl cyclopentanes has been developed involving Diels-Alder reaction of asymmetric dienes prepared from (+)-camphoric acid followed by aromatization of the resulting cyclohexene derivatives. Employing this protocol enantiospecific synthesis of (+)-herbertene and (+)-cuparene has been accomplished. (C) 2003 Elsevier Science Ltd. All rights reserved.