Synlett 2015; 26(04): 467-470
DOI: 10.1055/s-0034-1378924
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© Georg Thieme Verlag Stuttgart · New York

A Rapid and Stereocontrolled Synthesis of the Zizaane Ring System by Using an Intramolecular (4+3) Cycloaddition Reaction

Duchan R. Laplace
Department of Organic and Macromolecular Chemistry, Laboratory for Organic Synthesis, Ghent University, Krijgslaan 281 S4-bis, 9000 Ghent, Belgium   Fax: +32(9)2644998   Email: johan.winne@ugent.be
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Johan M. Winne*
Department of Organic and Macromolecular Chemistry, Laboratory for Organic Synthesis, Ghent University, Krijgslaan 281 S4-bis, 9000 Ghent, Belgium   Fax: +32(9)2644998   Email: johan.winne@ugent.be
› Author Affiliations
Further Information

Publication History

Received: 12 September 2014

Accepted after revision: 12 October 2014

Publication Date:
06 November 2014 (online)


Abstract

We report herein a very short synthetic approach to the tricyclo[6.2.1.01,5]undecane scaffold through a convergent and stereocontrolled route by using an intramolecular (4+3) cycloaddition of a simple furfuryl alcohol precursor with a pendant cyclopentadiene moiety. The formation of alternative reaction products under various conditions is also discussed.

Supporting Information