Applications of organocopper reagents in organic synthesis

Abstract

The importance of organocopper reagents in organic synthesis is highlighted and the different types of organocopper reagents available are briefly reviewed. Applications of organocopper reagents in the synthesis of natural products and related compounds of biological interest are then discussed commencing with synthetic approaches to thia-thromboxane analogues based on the organocopper conjugate addidon-enolate alkylation reaction. The extension of this methodology to the preparation of 2,3- disubstituted cyclopentenones, illustrated by the synthesis of the antimicrobial natural product, tetrahydrodicranenone B, is then discussed. Finally, synthetic applications of the organocopper alkyne addition reaction are described with emphasis on the use of double acetylene carbocupration for the stereospecific preparation of Z,Z-dienes. The use of this methodology for the synthesis of the Navel Orangeworm pheromone is discussed.