European Journal of Organic Chemistry

Synthesis of the Insect Pheromone (2S, 3S, 7RS)??Diprionyl Acetate by Diastereoselective Protonation

S Ebert, N Krause

Index: Ebert, Sophia; Krause, Norbert European Journal of Organic Chemistry, 2001 , # 20 p. 3831 - 3835

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Citation Number: 12

Abstract

Abstract The insect pheromone (2S, 3S, 7RS)-diprionyl acetate (1) was prepared from (S, S)- 2, 3-dimethylcyclohexanone (2), which in turn was obtained by the 1, 4-addition of lithium dimethylcuprate to (S)-(+)-carvone (3) and diastereoselective protonation of the resulting enolate with phenyl salicylate, followed by removal of the isopropenyl group and hydrogenation. Baeyer− Villiger rearrangement of (S, S)-2 and opening of the lactone (S, ...