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

Nayek, Abhijit ; Drew, Michael G. B. ; Ghosh, Subrata (2003) Convenient route to enantiopure aryl cyclopentanes via Diels-Alder reaction of asymmetric dienes. Total synthesis of (+)-herbertene (I) and (+)-cuparene Tetrahedron, 59 (26). pp. 5175-5181. ISSN 0040-4020

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...

Related URL: http://dx.doi.org/10.1016/S0040-4020(03)00807-X

Abstract

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.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Aromatization; Asymmetric Synthesis; Decarboxylation; Diels-alder Reactions; Terpenes and Terpenoids
ID Code:12384
Deposited On:10 Nov 2010 06:18
Last Modified:18 Feb 2011 12:19

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