Stereospecific Synthesis of (4E,10Z)-4,10-Tetradecadienyl Acetate, the Major Sex Pheromone of Apple Leaf Miner Moth, Phyllonorycter ringoniella

Title:Stereospecific Synthesis of (4E,10Z)-4,10-Tetradecadienyl Acetate, the Major Sex Pheromone of Apple Leaf Miner Moth, Phyllonorycter ringoniella

Volume: 18 Issue: 8

Author(s): Ramchandra Awalekar, Kishor Jagadhane, Shams Usmani, Shilpa Salunkhe, Dattatray Jamale, Shankar Hangirgekar, Govind Kolekar and Prashant Anbhule*

Affiliation:

• Medicinal Chemistry Research Laboratory, Department of Chemistry, Shivaji University, Kolhapur, 416004, M.S.,India

Keywords: Stereoselective synthesis, Apple leaf miner, Phyllonorycter ringoniella, Wittig olefination, Reduction, Gram scale synthesis, Green metrics calculations.

Abstract: The main component of the sex pheromone of many lepidopteran pests, (4E,10Z)-4,10- tetradecadienyl acetate (1) has been synthesized stereoselectively by using a simple route with 4- pentynol as a starting material. The stereoselective formation of the 4E double bond is based on the stereospecific reduction of internal alkyne with lithium aluminium hydride (LAH) while Wittig reaction was used to achieve 10Z double bond in the target pheromone component. The GC purity of the final acetate was achieved 97.87% while isomeric purities are more than 99%. The green chemistry principle shows a new concept towards the multistep pheromone synthesis via green metrics calculations.

Cite this article as:

Awalekar Ramchandra, Jagadhane Kishor, Usmani Shams, Salunkhe Shilpa , Jamale Dattatray, Hangirgekar Shankar, Kolekar Govind and Anbhule Prashant *, Stereospecific Synthesis of (4E,10Z)-4,10-Tetradecadienyl Acetate, the Major Sex Pheromone of Apple Leaf Miner Moth, Phyllonorycter ringoniella, Letters in Organic Chemistry 2021; 18 (8) . https://dx.doi.org/10.2174/1570178617999200922145900