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Synfacts 2007(7): 0741-0741  
DOI: 10.1055/s-2007-968639
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Intramolecular Cyclopropanation of Unsaturated Terminal Epoxides

Contributor(s): Paul Knochel, Andrei Gavryushin
D. M. Hodgson*, Y. K. Chung, I. Nuzzo, G. Freixas, K. K. Kulikievicz, E. Cleator, J.-M. Paris
University of Oxford and Merck Sharp and Dohme Ltd., Hoddesdon, UK; Rhodia Recherches, Saint Fons, France
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Publication History

Publication Date:
22 June 2007 (online)

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Significance

Fused cyclopropanes are structural features of many natural products and some new pharmaceutical agents. This elegant method utilizes the sequenced metallation of a terminal epoxide and the intramolecular attack of the resulting carbenoid species on the double bond. It allows a simple construction of various polycyclic structures having a cyclopropyl ring. Its utility for natural product synthesis was demonstrated by the simple preparation of (R)-β-cuparenone. The reaction can be done catalytically in TMP and is easily upscaled.