Efficient and stereo-selective syntheses of three stereoisomers of the sex pheromone of the cowpea weevil, Callosobruchus maculatus

Bioscience, Biotechnology and Biochemistry

Volumn 71, Issue 11, 2007, Pages 2720-2724

  Yajima, Arata ^a   Yamamoto, Masamichi ^a   Nukada, Tomoo ^a   Yabuta, Goro ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE   (Japan)

Author keywords

Callosobruchus maculatus; Cowpea weevil; Mild oxidation; Sex pheromone

Indexed keywords

CALLOSOBRUCHUS MACULATUS; COWPEA WEEVIL; MILD OXIDATION; SEX PHEROMONES; STEREOISOMERS; STEREOSELECTIVE SYNTHESIS;

INSECT CONTROL; ISOMERS; OXIDATION;

STEREOSELECTIVITY;

2,6 DIMETHYLOCTANE 1,8 DIOIC ACID; 2,6-DIMETHYLOCTANE-1,8-DIOIC ACID; 3 METHYLENE HEPTANOIC ACID; 3-METHYLENE-HEPTANOIC ACID; CARBOXYLIC ACID; DICARBOXYLIC ACID; SEX PHEROMONE; UNCLASSIFIED DRUG;

ANIMAL; ARTICLE; CHEMISTRY; METABOLISM; STEREOISOMERISM; SYNTHESIS; WEEVIL;

ANIMALS; CARBOXYLIC ACIDS; DICARBOXYLIC ACIDS; SEX ATTRACTANTS; STEREOISOMERISM; WEEVILS;

CALLOSOBRUCHUS MACULATUS;

EID: 36448945132     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.70309     Document Type: Article

References (28)

1. Southgate, B. J., Biology of the Bruchidae. Ann. Rev. Entomol., 24, 449-473 (1979).
2. Nojima, S., Shimomura, K., Honda, H., Yamamoto, I., and Ohsawa, K., Contact sex pheromone components of the cowpea weevil, Callosobruchus maculatus. J. Chem. Ecol., DOI 10.1007/s10886-007-9266-5.
3. Nakai, T., Yajima, A., Akasaka, K., Kaihoku, T., Ohtaki, M., Nukada, T., Ohrui, H., and Yabuta, G., Synthesis of the four stereoisomers of 2,6-dimethyloctane-1,8-dioic acid, a component of the copulation release pheromone of the cowpea weevil, Callosobruchus maculatus. Biosci. Biotechnol. Biochem., 69, 2401-2408 (2005).
4. Yajima, A., Akasaka, K., Nakai, T., Maehara, H., Ohrui, H., Nukada, T., and Yabuta, G., Direct determination of the stereoisomer constitution by 2D-HPLC and stereochemistry-pheromone activity relationship of the copulation release pheromone of the cowpea weevil, Callosobruchus maculatus. Tetrahedron, 62, 4590-4596 (2006).
5. Rup, P. J., and Sharma, S. P., Behavioural response of males and females of Callosobruchus maculatus to sex pheromone. Indian J. Ecol., 5, 72-76 (1978).
6. Qi, Y. T., and Burkholder, W. E., Sex pheromone biology and behavior of the cowpea weevil Callosobruchus maculatus (Coleoptera: Bruchidae). J. Chem. Ecol., 8, 527-534 (1982).
7. Ramaswamy, S. B., Shu, S., Monroe, W. A., and Mbata, G. N., Ultrastructure and potential role of integumentary glandular cells in adult male and female Callosobruchus subinnotatus (Pic) and C. maculatus (Fabricius) (Coleoptera: Bruchidae). Int. J. Insect Morphol. Embryol., 24, 51-61 (1995).
8. Phillips, T. W., Phillips, J. K., Webster, F. X., Tang, R., and Burkholder, W. E., Identification of sex pheromones from cowpea weevil, Callosobruchus maculatus, and related studies with C. analis (Coleoptera: Bruchidae). J. Chem. Ecol., 22, 2233-2249 (1996).
9. Fujisawa, T., Sato, T., Gotoh, Y., Kawashima, M., and Kawara, T., Reaction of diketene with Grignard reagents in the presence of cobalt catalyst. A convenient method for the synthesis of 3-methylenealkanoic acids leading to terpenoids. Bull. Chem. Soc. Jpn., 55, 3555-3559 (1982).
10. Yong, K. H., Lotoski, J. A., and Chong, J. M., Studies on the alkylation of 3-methyl-3-buten-1-ol dianion: an efficient synthesis of 3-methylene-1- alkanols including a San Jose scale sex pheromone. J. Org. Chem., 66, 8248-8251 (2001).
11. Dess, D. B., and Martin, J. C., Readily accessible 12-I-5 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones. J. Org. Chem., 48, 4155-4156 (1983).
12. Bal, B. S., Childers, Jr., W. E., and Pinnick, H. W., Oxidation of α,β-unsaturated aldehydes. Tetrahedron, 37, 2091-2096 (1981).
13. Rand, C. L., Van Horn, D. E., Moore, M. W., and Negishi, E., A versatile and selective route to difunctional trisubstituted (E)-alkene synthons via zirconium-catalyzed carboalumination of alkynes. J. Org. Chem., 46, 4093-4096 (1981).
14. Ma, S., and Negishi, E., Anti-carbometalation of homopropargyl alcohols and their higher homologues via nonchelation-controlled syn-carbometalation and chelation-controlled isomerization. J. Org. Chem., 62, 784-785 (1997).
15. Negishi, E., transition metal-catalyzed organometallic reactions that have revolutionized organic synthesis. Bull. Chem. Soc. Jpn., 80, 233-257 (2007).
16. Hayashi, T., Konishi, M., and Kumada, M., Dichloro-[1,1′- bis(diphenylphosphinoferrocene]palladium(II): an effective catalyst for cross-coupling reaction of a secondary alkyl Grignard reagent with organic halides. Tetrahedron Lett., 1871-1874 (1979).
17. Pinsker, O. A., Tsiklauri, P. G., and Grigoéva, N. Y., Highly stereoselective synthesis of a sex pheromone of the dry bean beetle Callosobruchus analis. Russ. Chem. Bull., 48, 1373-1375 (1999).
18. Grigoéva, N. Y., Tsiklauri, P. G., and Pinsker, O. A., An alternative synthesis of a sex pheromone of the dry bean beetle Callosobruchus analis. Russ. Chem. Bull., 48, 1376-1379 (1999).
19. Abarbri, M., Thibonnet, J., Parrain, J., and Duchêne, A., Palladium-catalyzed cross-coupling of iodovinylic acids with organometallic reagents. Selective synthesis of 3,3-disubstituted prop-2-enoic acids. Synthesis, 543-551 (2002).
20. Breitfelder, S., Schuemacher, A. C., Rölle, T., and Kikuchi, M., Hoffmann, R. W., Synthesis of pederic acid and related model studies. Helv. Chim. Acta, 87, 1202-1213 (2004).
21. Abe, Y., Goto, H., Sato, M., and Kato, T., Studies on ketene and its derivatives. CXV. Reaction of diketene with organometallics in the presence of the nickel- or palladium-phosphine complex. Chem. Pharm. Bull., 31, 1108-1111 (1983).
22. Abe, Y., Sato, M., Goto, H., Sugawara, R., Takahashi, E., and Kato, T., Studies on ketene and its derivatives. CXVIII. Nickel- or palladium-catalyzed reaction of diketene with organometallics. Synthesis of 3-substituted 3-butenoic acids. Chem. Pharm. Bull., 31, 4346-4354 (1983).
23. Bunce, R. A., Smith, C. L., and Lewis, J. R., Tetrahydro-1,5- benzoxazepines and tetrahydro-1H-1,5-benzodiazepines by a tandem reduction-reductive amination reaction. J. Heterocyclic Chem., 41, 963-970 (2004).
24. Vasil'ev, A. A., Kryshtal, G. V., and Serebryakov, E. P., A convenient protocol for the stereocontrolled synthesis of olefins with a homoallylic type of functionality. Mendeleev Commun., 41-42 (1995).
25. Vasil'ev, A. A., Vlasyuk, A. L., Gamalevich, G. D., and Serebryakov, E. P., A versatile convenient protocol for the stereocontrolled synthesis of olefinic insect pheromones. Bioorg. Med. Chem., 4, 389-400 (1996).
26. Shu, S., Koepnick, W. E., Mbata, G. N., Cork, A., and Ramaswamy, S. B., Sex pheromone production in Callosobruchus maculatus (Coleoptera: Bruchidae): electroantennographic and behavioral responses. J. Stored Prod. Res., 32, 21-30 (1996).
27. Cork, A., Hall, D. R., Blaney, W. M., and Simmonds, M. S. J., Identification of a component of the female sex pheromone of Callosobruchus analis (Coreoptera: Bruchidae). Tetrahedron Lett., 32, 129-132 (1991).
28. Shu, S., Mbata, G. N., Cork, A., and Ramaswamy, S. B., Sex pheromone of Callosobruchus subinnotatus. J. Chem. Ecol., 25, 2715-2727 (1999).