Pheromone synthesis, CLXXXI: Synthesis of the racemate and the enantiomers of (Z)-7,15-hexadecadien-4-olide, the sex pheromone of the yellowish elongate chafer, Heptophylla picea

Liebigs Annales

Volumn , Issue 5, 1997, Pages 839-843

  Nakayama, Tom ^a,b   Mori, Kenji ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

^b Earth Chemical Co Ltd

Author keywords

Chirality; Heptophylla picea; Lactones; Lipases; Pheromones; Yellowish elongate chafer

Indexed keywords

EID: 0342774146     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199719970508     Document Type: Article

References (23)

1. W. S. Leal, S. Kuwahara, M. Ono, S. Kubota, Bioorg. Med. Chem. 1996, 4, 315-321.
2. J. H. Tumlinson, M. G. Klein, R. E. Doolittle, T. L. Ladd, A. T. Proveaux, Science 1977, 197, 789-792.
3. W. S. Emerson, R. I. Longley, Jr., Org. Synth. 1963, Coll. Vol. 4, 302-303.
4. H. J. Bestmann, W. Stransky, O. Vostrowsky, Chem. Ber. 1976, 109, 1694-1700.
5. S.-K. Kang, W.-S. Kim, B.-H. Moon, Synthesis, 1985, 1161-1162.
6. G. Fouquet, M. Schlosser, Angew. Chem. 1974, 86, 50-51;
7. Angew. Chem. Int. Ed. Engl. 1974, 13, 82-83.
8. J. Sandri, J. Viala, Synth. Commun. 1992, 22, 2945-2948.
9. A. Pommier, J-M. Pons, P. J. Kocienski, J. Org. Chem. 1995, 60, 7334-7339.
10. K. Fuji, M. Node, S. Terada, M. Murata, H. Nagasawa, T. Taga, K. Machida, J. Am. Chem. Soc. 1985, 107, 6404-6406.
11. F. Moriuchi, H. Muroi, H. Aibe, Chem. Lett. 1987, 1141-1144.
12. A. Sakamoto, Y. Yamamoto, J. Oda, J. Am. Chem. Soc. 1987, 109, 7188-7189.
13. A. L. Gutman, T. Bravdo, J. Org. Chem. 1989, 54, 4263-4265.
14. A. L. Gutman, K. Zuobi, A. Boltansky, Tetrahedron Lett. 1987, 25, 3861-3864.
15. L. Blanco, E. Guibé-Jampel, G. Rousseau, Tetrahedron Lett. 1988, 29, 1915-1918.
16. E. Guibé-Jampel, G. Rousseau, L. Blanco, Tetrahedron Lett. 1989, 30, 67-68.
17. Y. Koichi, K. Suginaka, Y. Yamamoto, J. Chem. Soc., Perkin Trans. 1 1995, 1645-1646.
18. M. Huffer, P. Schreier, Tetrahedron: Asymmetry 1991, 2, 1157-1164.
19. A. Mosandl, C. Günther, J. Agric. Food Chem. 1989, 37, 413-418.
20. E. Fukusaki, S. Senda, Y. Nakazono, T. Omata, Tetrahedron 1991, 32, 6223-6230.
21. A. Kharrat, C. Gardrat, B. Maillard, Can. J. Chem. 1985, 63, 2522-2528.
22. M. Jacobson, I. Keiser, D. L. Chambers, D. H. Miyashita, C. Hardinc, J. Med. Chem. 1971, 14, 236-239.
23. D. K. Johnson, J. Donohoe, J. Kang, Synth. Commun. 1994, 24, 1557-1564.