79090-63-4

Upstream product

• 53735-49-2 (R)-(+)-1-undecyn-3-ol 
• 188349-85-1 Acetic acid (R)-1-trimethylsilanylethynyl-nonyl ester 
• 79120-88-0 (R)-(-)-ethyl 3,4-tridecadienoate 
• 79120-90-4 (R)-(-)-3,4-tridecadien-1-ol 
• 98-59-9 p-toluenesulfonyl chloride 
• 79120-90-4 (S)-(+)-3,4-tridecadien-1-ol 

Downstream Products

• 28066-21-9 (E)-(S)-(+)-methyl 2,4,5-tetradecatrienoate 
• 60705-57-9 (R)-methyl 2-phenylseleno-4,5-tetradecadienoate 

Relevant academic research and scientific papers

Pheromone synthesis. Part 249: Syntheses of methyl (R,E)-2,4,5- tetradecatrienoate and methyl (2E,4Z)-2,4-decadienoate, the pheromone components of the male dried bean beetle, Acanthoscelides obtectus (Say)

The enantiomers of methyl (E)-2,4,5-tetradecatrienoate (1), a component of the male pheromone of Acanthoscelides obtectus, were synthesized from the enantiomers of 1-undecyn-3-ol (6), which were obtained via asymmetric acetylation of (±)-1-trimethylsilyl-1-undecyn-3-ol (4) with vinyl acetate as catalyzed by lipase PS (Amano). The ortho ester Claisen rearrangement of 6 with triethyl orthoacetate was the key-step to generate the chiral allenic system. A new synthesis of (±)-1 was also executed starting from (±)-6. Three different syntheses of methyl (2E,4Z)-2,4-decadienoate (2), another component of the male pheromone of A. obtectus, were achieved by means of either palladium-catalyzed Heck reaction or a Claisen and an Al 2O3 catalyzed thermal rearrangements.

SYNTHESIS OF OPTICALLY ACTIVE FORMS OF METHYL (E)-2,4,5-TETRADECATRIENOATE, THE PHEROMONE OF THE MALE DRIED BEAN BEETLE

Both enantiomers of methyl (E)-2,4,5,-tetradecatrienoate were synthesized with 125-127percent the rotatory power of the natural product which was isolated as the pheromone of Acanthoscelides obtectus.The absolute configuration of the levorotatory natural pheromone was confirmed to be R.