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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 9, 1979 - Issue 4
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Original Articles

Addition of Organocuprates to Cyclobutenyl Esters. Synthesis of (±)-Grandisol

Pages 325-331 | Received 14 Oct 1978, Published online: 05 Dec 2006
 

Abstract

The conjugate addition of organocuprates to certain esters2, methylene lactones3, and enol lactones4 has been demonstrated. We report herein that cyclobutenyl esters readily undergo conjugate addition with these reagents, and that this reaction has been used to synthesize the boll weevil pheromone (±)-grandisol (18).5

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