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

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

Journal Name: Letters in Organic Chemistry

Volume 18 , Issue 8 , 2021


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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.

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

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Article Details

VOLUME: 18
ISSUE: 8
Year: 2021
Published on: 22 September, 2020
Page: [588 - 593]
Pages: 6
DOI: 10.2174/1570178617999200922145900
Price: $65

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