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)

Tetrahedron

Volumn 68, Issue 7, 2012, Pages 1936-1946

  Mori, Kenji ^a  

^a TOYO GOSEI CO LTD   (Japan)

Author keywords

Acanthoscelides obtectus (Say); Allene; Claisen rearrangement; Heck reaction; Lipase; Optically active allene; Pheromone

Indexed keywords

(DEXTRO LEVO) 1 IODO 1,2 UNDECADIENE; (DEXTRO LEVO) METHYL 2,4,5 TETRADECATRIENOATE; (DEXTRO LEVO) METHYL 3,4 DECADIENOATE; 1 UNDECYN 3 OL; 3,4 TRIDECADIENYL TOSYLATE; 4,5 TETRADECADIENOIC ACID; ETHYL 3,4 TRIDECADIENOATE; LEVO DEXTRO 1 TRIMETHYLSILYL 1 UNDECYN 3 OL; METHYL 2 PHENYLSELENO 4,5 TETRADECADIENOATE; METHYL 2,4 DECADIENOATE; METHYL 4,5 TETRADECADIENOATE; PALLADIUM; PHEROMONE; TETRADECA 2,4,5 TRIENOIC ACID METHYL ESTER; TRIACYLGLYCEROL LIPASE; TRIETHYL ORTHOACETATE; UNCLASSIFIED DRUG; VINYL ACETATE;

ACANTHOSCELIDES OBTECTUS; ACETYLATION; ANIMAL EXPERIMENT; ARTICLE; BEETLE; CHEMICAL STRUCTURE; CLAISEN REARRANGEMENT; ENANTIOMER; HECK REACTION; HORMONE SYNTHESIS; NONHUMAN; PRIORITY JOURNAL;

ACANTHOSCELIDES OBTECTUS; COLEOPTERA;

EID: 84856403591     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.12.064     Document Type: Article

References (33)

1. Shikichi, Y; Mori, K. Biosci. Biotechnol. Biochem., in press.
2. D.F. Horler J. Chem. Soc. C 1970 859 862
3. P.D. Landor, S.R. Landor, and S. Mukasa J. Chem. Soc., Chem. Commun. 1971 1638 1639
4. K. Mori J. ApSimon, The Total Synthesis of Natural Products Vol. 4 1981 Wiley New York, NY 55 57
5. K. Mori J. ApSimon, The Total Synthesis of Natural Products Vol. 9 1992 Wiley New York, NY 212 215
6. W.H. Pirkle, and C.W. Boeder J. Org. Chem. 43 1978 2091 2093
7. K. Mori, T. Nukada, and T. Ebata Tetrahedron 37 1981 1343 1347
8. A.C. Oehlschlager, and E. Czyzewska Tetrahedron Lett. 24 1983 5587 5590
9. T. Fujisawa, S. Iida, and T. Sato Tetrahedron Lett. 25 1984 4007 4010
10. M. Franck-Neunann, D. Martina, and D. Neff Tetrahedron: Asymmetry 9 1998 697 708
11. K. Mori J.G. Millar, K.F. Haynes, Methods in Chemical Ecology: Chemical Methods Vol. 1 1998 Kluwer Norwell, MA 295 338
12. P. Allevi, P. Ciuffreda, and M. Anastasia Tetrahedron: Asymmetry 8 1997 93 99
13. Y. Masuda, and K. Mori Eur. J. Org. Chem. 2005 4789 4800
14. T. Kato, K. Ishigami, K. Akasaka, and H. Watanabe Tetrahedron 65 2009 6953 6958
15. R. Bovara, G. Carrea, L. Ferrara, and S. Riva Tetrahedron: Asymmetry 2 1991 931 938
16. S. Tamogami, K. Awano, M. Amaike, Y. Takagi, and T. Kitahara Flavour Fragrance J. 16 2001 349 352
17. P.J. Kocienski, G. Cernigliaro, and G. Feldstein J. Org. Chem. 42 1977 353 355
18. K. Mori Bioorg. Med. Chem. 15 2007 7505 7523
19. K. Mori Chirality 23 2011 449 462
20. K. Mori Chim. Oggi/Chem. Today 29 2011 40 43
21. B.D. Sherry, and F.D. Toste J. Am. Chem. Soc. 126 2004 15978 15979
22. D. Garayalde, E. Gómez-Bengoa, X. Huang, A. Goeke, and C. Nevado J. Am. Chem. Soc. 132 2010 4720 4730
23. J.W. Grissom, D. Klingberg, D. Huang, and B.J. Slattery J. Org. Chem. 62 1997 603 626
24. P. Rona, and P. Crabbé J. Am. Chem. Soc. 90 1968 4733 4734
25. R. Riverios, D. Rodríguez, J.P. Sestelo, and R.A. Sarandeses Org. Lett. 8 2006 1403 1406
26. R. Boudouy, and J. Gore Synthesis 1974 573 574
27. E.J. Corey, N.W. Gilman, and B.E. Ganem J. Am. Chem. Soc. 90 1968 5616 5617
28. A. Claesson, and L.-I. Olsson J. Chem. Soc., Chem. Commun. 1979 524 525
29. T. Jeffery Tetrahedron Lett. 26 1985 2667 2670
30. T. Jeffery Synthesis 1987 70 71
31. C. Lüthy, P. Konstantin, and K.G. Untch J. Am. Chem. Soc. 100 1978 6211 6217
32. S. Tsuboi, T. Masuda, and A. Takeda J. Org. Chem. 47 1982 4478 4482
33. S. Tsuboi, T. Masuda, S. Mimura, and A. Takeda Organic Syntheses Collect. Vol. 8 1993 Wiley New York, NY 251-254