Tetrahedron

Syntheses with sulfones XLIX: stereo-and enantioselective synthesis of (s)-(-)-3, 9-dimethyl 6-(1-methylethyl)(e)-5, 8-decadien 1-ol acetate, sexual pheromone of …

E Alvarez, T Cuvigny, CH du Penhoat, M Julia

Index: Alvarez, E.; Cuvigny, C.; Herve du Penhoat, C.; Julia, M. Tetrahedron, 1988 , vol. 44, # 1 p. 119 - 126

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Citation Number: 56

Abstract

The stereo-and enantioselective synthesis of the yellow scale pheromone,(S)-(-)-3, 9- dimethyl 6-(1-methylethyl)(E)-5, 8-decadien 1-ol acetate, from 3-(R)(̃+)-valerolactone 5 and [(4-methyl 3-pentenyl) sulfonyl] benzene 8 is described. The key step is the introduction of the isopropyl group by the stereoselective cross-coupling reaction of the dienesulfone 12 with isopropylmagnesium chloride in the presence of FeCl3.

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