Leucoptera coffeella

A three-step synthesis of a mixture of stereoisomers of 5,9 -dimethylpentadecane, the sex pheromone of the coffee leaf miner, Leucoptera coffeella, has been described. The key step being the unsymmetrical Wittig olefination to build the carbon skeleton of the molecule. 

Moreira, J.A. and Correa, A.G. (2003). Enantioselective synthesis of three stereoisomers of 5,9-dimethylpentadecane, sex pheromone component of Leucoptera coffeella, from (-)-isopulegol. Tetrahedron Asymm., 14, 3787-3795. 

Zarbin, P.H.G., Princival, J.L., de Lima, E.R., dos Santos, A.A., Ambrogio, B.G. and de Oliveira, A.R.M. (2004). Unsymmetrical double Wittig olefination in the syntheses of insect pheromones. Part 1 synthesis of 5,9-dimethylpentadecane, the sexual pheromone of Leucoptera coffeella. Tetrahedron Lett., 45, 239-241. 

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