原创力文档synthesis of highly functionalised enantiopure bicyclo[3.2.1]- octane systems from carvone合成的高functionalised enantiopure bicyclo香芹酮(3.2.1)-辛烷系统.pdfVIP
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synthesis of highly functionalised enantiopure bicyclo[3.2.1]- octane systems from carvone合成的高functionalised enantiopure bicyclo香芹酮(3.2.1)-辛烷系统
Molecules 2004, 9, 287-299
molecules
ISSN 1420-3049
Synthesis of Highly Functionalised Enantiopure Bicyclo[3.2.1]-
octane Systems from Carvone
Antonio Abad *, Consuelo Agulló, Ana C. Cuñat *, Ignacio de Alfonso, Ismael Navarro and
Noelia Vera.
Departamento de Química Orgánica. Facultad de Ciencias Químicas. Dr. Moliner, 50, 46100-Burjasot,
(Valencia), Spain. Tel. (+34) 96 3544509/3543038. Fax: (+34) 96 3544328.
*Authors to whom correspondence should be addressed; e-mail: antonio.abad@uv.es;
ana.cunat@uv.es
Received: 2 February 2004 / Accepted: 8 March 2004 / Published: 30 April 2004
Abstract: The commercially available monoterpene carvone has been efficiently converted
into the tricyclo[2.7]octane and bicyclo[3.2.1]octane systems characteristic of some
biologically active compounds. The sequence used for this transformation involves as key
features an intramolecular Diels-Alder reaction of a 5-vinyl-1,3-cyclohexadiene and a
cyclopropane ring opening.
Keywords: Carvone, Diels-Alder reaction, cyclopropane cleavage, 5-vinyl-1,3-
cyclohexadiene, samarium diiodide, bicyclo[3.2.1]octane, tricyclo[2.7]octane
Introduction
The bicyclo[3.2.1]octane ring system is the basic framework of many important biologically active
natural compounds, particularly tri- and tetracyclic sesqui- and diterpenes [1]. The widespread
occurrence of this common structural motif in so many biologically active natural products has
stimulated the preparation of simple non-natural structures containing the carbo-bicyclic system with
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