Improved Synthesis of (3E,7Z)-3,7-Tetradecadienyl Acetate, the Major Sex Pheromone Constituent of the Potato Pest Symmetrischema tangolias (Gyen)

Abstract

An efficient six-step synthesis of (3E,7Z)-3,7-tetradecadienyl acetate, the major component of the sex pheromone of the potato pest Symmetrischema tangolias (Gyen), is described, starting from the commercially available dihydropyran. The stereoselective formation of the 7Z double bond is accomplished by a Wittig reaction, while the 3E double bond is formed by a modified Knoevenagel condensation. The overall yield of the synthesis is 28%, giving the final product in high stereochemical purity (95%). The simplicity and the low cost of the herein reported synthesis suggest the potential practical use of the above pheromone in integrated management programs, for this serious insect pest.

Facile and Efficient Syntheses of (11Z,13Z)-Hexadecadienal and Its Derivatives: Key Sex Pheromone and Attractant Components of Notodontidae

“…Wittig reactions are most commonly used to couple aldehydes to singly-substituted phosphine ylides. Unstabilized ylides, mainly via the erythro betaine intermediate, lead to the Z -alkene product [29,32,33]. The carbonyl olefination of the alkynal 6 with phosphorus ylides is a general method for the preparation of Z -enyne 7 .…”

Synthesis and bioactivity of (13Z,15E)‐octadecadienal: A sex pheromone component from Micromelalopha siversi Staudinger (Lepidoptera: Notodontidae)

“…[38][39][40][41] In the normal Wittig reaction, the unstabilized ylides are produced primarily through those erythro betaine intermediates, resulting in the production of Z-alkene products. [42][43][44] By contrast, the E-alkene products are mainly produced by the Wittig-Schlosser reaction via the threo betaine intermediates. [45][46][47] Accordingly, in this study, the E configuration of the enyne and diene were constructed by the Wittig-Schlosser condition, 45 whereas the Z configurations were prepared through the normal Wittig reaction.…”

A Concise Li/liq. NH3Mediated Synthesis of (4E,10Z)-Tetradeca-4,10-dienyl Acetate: The Major Sex Pheromone of Apple Leafminer Moth, Phyllonorycter ringoniella

“…All the intermediates prepared in this approach and the procedures described so far are convenient and can be used in many other pheromone syntheses of similar structures from Phyllonorycter genus of moths (in the family Gracillariidae) and also from various insect families. Finally, acetylation 7,12 was performed on the primary alcohol 10 using acetic anhydride and pyridine in CH 2 Cl 2 to afford final pheromone 1 in 98% yield and was confirmed by IR, GC-MS, 1 H NMR,…”