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

Bioscience, Biotechnology and Biochemistry

Volumn 67, Issue 10, 2003, Pages 2224-2231

  Mori, Kenji ^a  

^a Fuji Flavor Co Ltd   (Japan)

Author keywords

Cochliomyia hominivorax; Methyl branched ketone; Methyl branched secondary acetate; Pheromone; Screwworm fly

Indexed keywords

COCHLIOMYIA; COCHLIOMYIA HOMINIVORAX;

21 METHYL 7 HENTRIACONTANONE; 21-METHYL-7-HENTRIACONTANONE; 5 ACETOXY 19 METHYLNONACOSANE; 5-ACETOXY-19-METHYLNONACOSANE; CITRONELLOL; HYDROCARBON; KETONE; SEX PHEROMONE; TERPENE;

ANIMAL; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; FEMALE; FLY; MALE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANIMALS; DIPTERA; FEMALE; HYDROCARBONS; KETONES; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MOLECULAR STRUCTURE; MONOTERPENES; SEX ATTRACTANTS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 3142730921     PISSN: 09168451     EISSN: None     Source Type: Journal    
DOI: 10.1271/bbb.67.2224     Document Type: Article

References (7)

1. Pomonis, J. G., Hammack, L., and Hakk, H., Identification of compounds in an HPLC fraction from female extracts that elicit mating responses in male screwworm flies, Cochliomyia hominivorax. J. Chem. Ecol., 19, 985-1007 (1993).
2. Furukawa, A., Shibata, C., and Mori, K., Synthesis of four methyl-branched secondary acetates and a methyl-branched ketone as possible candidates for the female pheromone of the screwworm fly, Cochliomyia hominivorax. Biosci. Biotechnol. Biochem., 66, 1164-1169 (2002).
3. Carlson, D. A., Berkebile, D. R., Skoda, S. R., and Mori, K., New world screwworm sex stimulant: Bioactivity of synthetics. Naturwissenschaften, in press.
4. Shirai, Y., Seki, M., and Mori, K., Pheromone synthesis, CXCIX. Synthesis of all the stereoisomers of 7-methylheptadecane and 7,11-dimethylheptadecane, the female sex pheromone components of the spring hemlock looper and the pitch pine looper. Eur. J. Org. Chem., 3139-3145 (1999).
5. Fouquet, C., and Schlosser, M., Improved carbon-carbon linking by controlled copper catalysis. Angew. Chem. Int. Ed. Engl., 13, 82-83 (1974).
6. Ohrui, H., Terashima, H., Imaizumi, K., and Akasaka, K., A solution of the "intrinsic problem" of diastereomer method in chiral discrimination. Development of a method for highly efficient and sensitive discrimination of chiral alcohols. Proc. Japan Acad., 78, Ser. B, 69-72 (2002).
7. Tashiro, T., Akasaka, K., Ohrui, H., Fattorusso, E., and Mori, K., Determination of the absolute configuration at the two cyclopropane moieties of plakoside A, an immunosuppressive marine galactosphingolipid. Eur. J. Org. Chem., 3659-3665 (2002).