Synthesis of the enantiomers of 21-methyl-7-hentriacontanone and a stereoisomeric mixture of 5-acetoxy-19-methylnonacosane, candidates for the female sex pheromone of the screwworm fly Cochliomyia hominivorax.
The enantiomers of 21-methyl-7-hentriacontanone (1), which might show weak bioactivity as the female sex pheromone of the screwworm fly (Cochliomyia hominivorax), were synthesized by starting from the enantiomers of citronellal. (+/-)-Citronellol was converted to a racemic and diastereomeric mixture of 5-acetoxy-19-methylnonacosane (2), which was considered to be a candidate for the female sex pheromone of C. hominivorax. Synthetic 2 exhibited no pheromone activity against male C. hominivorax.
Mori
Kenji
K
Insect Pheromone and Traps Division, Fuji Flavor Co., Ltd., Midorigaoka, Hamura-City, Tokyo, Japan.
D000080462:Acyclic Monoterpenes; D000818:Animals; D004175:Diptera / Q000737:chemistry*; D005260:Female; D006838:Hydrocarbons / Q000138:chemical synthesis / Q000494:pharmacology; D007659:Ketones / Q000138:chemical synthesis / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D015394:Molecular Structure; D039821:Monoterpenes / Q000737:chemistry; D012724:Sex Attractants / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
C487924:21-methyl-7-hentriacontanone; C487925:5-acetoxy-19-methylnonacosane; D000080462:Acyclic Monoterpenes; D006838:Hydrocarbons; D007659:Ketones; D039821:Monoterpenes; D012724:Sex Attractants; C007078:citronellol