Tetrahedron letters

Unsymmetrical double Wittig olefination on the syntheses of insect pheromones. Part 1: Synthesis of 5, 9-dimethylpentadecane, the sexual pheromone of Leucoptera …

PHG Zarbin, JL Princival, ER de Lima, AA dos Santos…

Index: Zarbin, Paulo H. G.; Princival, Jefferson L.; De Lima, Eraldo R.; Dos Santos, Alcindo A.; Ambrogio, Bianca G.; De Oliveira, Alfredo R. M. Tetrahedron Letters, 2004 , vol. 45, # 2 p. 239 - 241

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Citation Number: 25

Abstract

An expeditious three-step synthesis of a mixture of stereoisomers of 5, 9- dimethylpentadecane, the sexual pheromone of the coffee leaf miner Leucoptera coffeella, is described. The route employs an unsymmetrical double Wittig olefination to build the carbon skeleton of the molecule, as the key reaction. The bis-phosphonium salt, derived from 1, 3-dibromopropane, reacted 'one-pot'with the ketones 2-octanone and 2-hexanone, ...