A Facile Asymmetric Synthesis of (S)-14-Methyl-1-Octadecene, the Sex Pheromone of the Peach Leafminer Moth

Tao Zhang,Wei-Li Ma,Zhen-Ting Du,Tian-Rui Li,Jun-Run Wang,Jia Wu

doi:10.3390/molecules18055201

Abstract

An asymmetric synthesis of 14-methyl-1-octadecene, the sex pheromone of the peach leafminer moth has been achieved. The target molecule was synthesized in six linear steps and in 30.3% overall yield from commercially available hexanoyl chloride, (S)-4-benzyloxazolidin-2-one and 1,9-nonanediol. The hexanoyl chloride was connected with (S)-4-benzyloxazolidin-2-one, and with the induction of the chiral oxazolidinone auxiliary, after chiral methylation, LAH reduction and then tosylation gave the chiral key intermediate 5 in high stereoselectivity. 1,9-Nonanediol, was selectively brominated, THP protected and subjected to Li2CuCl4-mediated C-C coupling to afford a C12 intermediate. The target molecule, (S)-14-methyl-1-octadecene, was obtained after the two parts were subjected to a second Li2CuCl4-mediated C-C coupling. Our synthetic approach represents the first time a substrate-control asymmetric synthesis of (S)-14-methyl-1-octadecene has been reported.

Highlights

Nowadays, there is a sharp conflict between intense agricultural production and environmental issues
We all are facing a big challenge caused by the detrimental effects resulting from traditional agricultural production [1], there is an urgent need to develop more green production modes, such as the use of environmentally benign, low-dosage sex pheromones to control pests [2,3]
This mode plays an important role in so-called Integrated Pest Management (IPM)

Summary

Introduction

There is a sharp conflict between intense agricultural production and environmental issues. We all are facing a big challenge caused by the detrimental effects resulting from traditional agricultural production [1], there is an urgent need to develop more green production modes, such as the use of environmentally benign, low-dosage sex pheromones to control pests [2,3]. This mode plays an important role in so-called Integrated Pest Management (IPM). We wish to report a synthesis of (S)-14-methyl-1-octadecene (1) from inexpensive starting materials by a substrate-induction strategy

Results and Discussion

Experimental

Conclusions