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Synthesis 2007(7): 999-1002  
DOI: 10.1055/s-2007-965951
PAPER
© Georg Thieme Verlag Stuttgart · New York

Convenient Formal Synthesis of (±)-Cuparene, (±)-Enokipodins A and B, and (±)-Cuparene-1,4-Quinone

Francesco Seccia,b, Angelo Frongiab, Jean Ollivier*a, Pier Paolo Piras*b
a Laboratoire de Synthèse organique et Méthodologie, UMR 8182, Institut de Chimie Moléculaire et des Matériaux d’Orsay, Université Paris-Sud, 91405 Orsay, France
Fax: +33(1)69156278; e-Mail: jollivie@icmo.u-psud.fr;
b Dipartimento di Scienze Chimiche, Università di Cagliari, Complesso Universitario di Monserrato, S.S. 554, Bivio per Sestu, 09042 Monserrato, Cagliari, Italy
Fax: +39(070)6754388; e-Mail: pppiras@unica.it ;
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Publication History

Received 21 November 2006
Publication Date:
20 February 2007 (online)

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Abstract

A Brønsted or Lewis acid mediated semi-pinacolic rearrangement effected on the diastereomers of cyclobutanol derivatives leads efficiently to useful intermediates in the synthesis of cuparene-type sesquiterpenes. The cyclobutanols are themselves easily obtainable from cyclopropyl phenyl sulfide.

Key words

antifugal agents - aldol reactions - rearrangements - ring expansion - ketones