Selenoesters in organic synthesis. 2. New synthesis of saturated and ?,?-unsaturated ketones and the synthesis of the Peach moth pheromone (Carposia niponensis)

Abstract

1. Selenoesters react readily with a wide variety of organometallic reagents to give saturated ketones in high yields. 2. Treatment of alkenyl copper (I) derivatives with selenoesters (or chloroanhydrides) in the presence of hexamethylphosphoramide gives excellent yields of α,β-unsaturated ketones of varying structures. 3. The syntheses of the components of the Peach moth pheromoneCarposia niponensis, namely, Z-12-nonadecen-9-one and Z-13-eicosen-10-one, have been described.