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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

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To link to this item 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.

Item Type:Article
Refereed:Yes
Divisions:Faculty of Life Sciences > School of Chemistry, Food and Pharmacy > Department of Chemistry
ID Code:11528
Uncontrolled Keywords:aromatization, asymmetric synthesis, decarboxylation, Diels-Alder reactions, terpenes and terpenoids , VICINALLY SUBSTITUTED CYCLOPENTANONES, ENANTIOSELECTIVE RING CONSTRUCTION, CHIRAL BICYCLIC LACTAMS, NATURAL SESQUITERPENOIDS, STEREOCONTROLLED APPROACH, CUPARENE SESQUITERPENES, COMMON INTERMEDIATE, QUATERNARY CARBONS, FORMAL SYNTHESIS, REARRANGEMENT

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