Electrocyclic Ring-Opening Reactions of gem-Dibromocyclopropanes in the Synthesis of Natural Products and Related Compounds

Brian Halton; Joanne Harvey

doi:10.1055/s-2006-948193

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Synlett 2006(13): 1975-2000
DOI: 10.1055/s-2006-948193

ACCOUNT

Electrocyclic Ring-Opening Reactions of gem-Dibromocyclopropanes in the Synthesis of Natural Products and Related Compounds

Brian Halton, Joanne Harvey*
School of Chemical and Physical Sciences, Victoria University of Wellington, PO Box 600, Wellington, New Zealand
e-Mail: brian.halton@vuw.ac.nz; e-Mail: joanne.harvey@vuw.ac.nz;

Further Information

Publication History

Received 22 March 2006
Publication Date:
09 August 2006 (online)

Abstract
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Abstract

The disrotatory ring opening of gem-dibromocyclopropanes provides a versatile and increasingly utilised procedure for the synthesis of a range of natural products. The field is summarised and product formation explained.

1 Introduction
2 Selected Uses of gem-Dibromocyclopropanes
2.1 Via the Lithium Bromocarbenoid
2.2 Via the 1-Bromocyclopropene
2.3 Miscellaneous Transformations
3 The Cyclopropyl-to-Allyl Rearrangement
3.1 Mechanistic Aspects
3.2 Thermal Reactions
3.3 Reactions in the Presence of an External Nucleophile
3.3.1 Non-Annelated gem-Dibromocyclopropanes
3.3.2 Medium-to-Large Ring-Fused gem-Dibromocyclopropanes
3.3.3 7,7-Dibromobicyclo[4.1.0]heptanes
3.3.4 6,6-Dibromobicyclo[3.1.0]hexanes
3.4 Reactions in the Presence of an Internal Nucleophile
3.4.1 Attached Directly to the Cyclopropane
3.4.2 Attached to a Remote Centre

Key words

dibromocyclopropanes - disrotatory openings - allylic cations - natural products - total synthesis

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Special issue on cyclopropanes and related rings: Chem. Rev.; 2003, 103 (4).

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Banwell, M. G.; Ma, X. 2006, in preparation. We thank Professor Banwell for providing this information prior to publication.