Title:Utility of Unsaturated Terminal Epoxides in Cyclopropane Synthesis
VOLUME: 20 ISSUE: 1
Author(s):David M. Hodgson and Saifullah Salik
Affiliation:Department of Chemistry, Chemistry Research Laboratory, University of Oxford, OX1 3TA, UK.
Keywords:Cyclopropanes, epoxide, intramolecular cyclopropanation, lithium 2, 2, 6, 6-tetramethylpiperidide,
total synthesis.
Abstract:Developments in the synthesis of bicyclo[n.1.0]alkanes by lithium 2,2,6,6-tetramethylpiperidide-induced
intramolecular cyclopropanation of unsaturated terminal epoxides are reviewed. The main alternative intramolecular
cyclopropanation strategies are also briefly discussed to put the epoxide chemistry in perspective. Terminal epoxide
(or chlorohydrin) precursors possessing a tethered alkene undergo intramolecular cyclopropanation with
complete stereoselectivity and in generally good to excellent yields to give cyclopropyl alcohols; application of this
cyclopropanation methodology in the synthesis of natural products is also reviewed.
