A Total and Convergent Synthesis of (7Z,11Z,13E)-7,11,13-Hexadecatrienal, the Major Sex Pheromone Component of the Citrus Leafminer, Phyllocnistis citrella

Abstract (Z, Z, E)-7, 11, 13-Hexadecatrienal, the major component of the sex pheromone of the citrus leaf miner Phyllocnistis citrella is efficiently and stereoselectively synthesized starting from the commercially available 6-Bromo-1-hexanol and described hereby. The synthesis of (Z, Z, E)-7, 11, 13-Hexadecatrienal was carried out by using the key step being Wittig reaction of the protected ylide using potassium tertiary butoxide a base to furnish 11Z double bond (Z)-isomer as the major product. The stereoselective formation of the 7Z double bond is formed by the stereospecific reduction of internal alkyne with sodium borohydride (PIINi). The synthetic methodology is inexpensive with its operational simplicity and it will be attractive for academic and industrial research.