Intramolecular [2+2] photocycloadditions as an approach towards the bicyclo[2.1.1]hexane substructure of solanoeclepin A

Richard H. Blaauw; Jean-François Brière; Remco de Jong; Jorg C. J. Benningshof; Angeline E. van Ginkel; Floris P. J. T. Rutjes; Jan Fraanje; Kees Goubitz; Henk Schenk; Henk Hiemstra

doi:10.1039/B003755I

Intramolecular [2+2] photocycloadditions as an approach towards the bicyclo[2.1.1]hexane substructure of solanoeclepin A

Richard H. Blaauw,^a Jean-François Brière,^a Remco de Jong,^a Jorg C. J. Benningshof,^a Angeline E. van Ginkel,^a Floris P. J. T. Rutjes,^a Jan Fraanje,†^a Kees Goubitz,†^a Henk Schenk †^a and Henk Hiemstra*^a

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^a Institute of Molecular Chemistry, Laboratories of Organic Chemistry and Crystallography, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS, Amsterdam., E-mail: henkh@org.chem.uva.nl

Abstract

The synthesis of a tricyclic substructure of solanoeclepin A is described. The key step involves an intramolecular [2+2] photocycloaddition between a dioxinone and a tetrasubstituted bicyclic alkene providing the strained bicyclo[2.1.1]hexane moiety.

Chemical Communications

Intramolecular [2+2] photocycloadditions as an approach towards the bicyclo[2.1.1]hexane substructure of solanoeclepin A

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Intramolecular [2+2] photocycloadditions as an approach towards the bicyclo[2.1.1]hexane substructure of solanoeclepin A

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