A concise synthesis of the sex pheromones of pine sawflies

Chinese Journal of Organic Chemistry

Volumn 27, Issue 7, 2007, Pages 866-869

  Wang, Zi Kun ^a   Tian, Wei Sheng ^b   Pan, Xin Fu ^a  

^a LANZHOU UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Coupling reaction; Methyl (R) 5 bromo 4 methylpentanoate; Sex pheromone of Pine sawfly

Indexed keywords

EID: 34548319189     PISSN: 02532786     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (25)

1. Coppel, H. C.; Casida, J. E.; Dauterman, W. C. An. Entomol. Soc. Am. 1960, 53, 510.
2. Jewett, D. M.; Matsumura, F.; Coppel, H. C. Science 1976, 192, 51.
3. (a) Tai, A.; Morimoto, N.; Yoshikawa, M.; Uehara, K.; Sugimara, T.; Kikukawa, T. Agric. Biol. Chem. 1990, 54, 1753.
4. (b) Hedenström, E.; Högberg, H. E.; Wassgren, A. B.; Bergström, G.; Löfqvist, J.; Hansson, B. S.; Anderbrant, O. Tetrahedron 1992, 48, 3139.
5. For racemic syntheses of 1, see: (a) Reference 2.
6. (b) Magnusson, G. Tetrahedron Lett. 1977, 31, 2713.
7. (c) Kocienski, P. J.; Ansell, J. M. J. Org. Chem. 1977, 42, 1102.
8. (d) Place, P.; Roumestant, M. L.; Gore, J. J. Org. Chem. 1978, 43, 1001.
9. (e) Baker, R.; Winton, P. M. Tetrahedron Lett. 1980, 21, 1175.
10. (f) Kallmerten, J.; Balestra, M. J. Org. Chem. 1986, 51, 2855.
11. (g) Gould, T. J.; Balesstra, M.; Wittman, M. D.; Gary, J. A.; Rossano, L. T.; Kallmerten, J. J. Org. Chem. 1987, 52, 3889.
12. (h) Hedenström, E.; Högberg, H. E. Tetrahedron 1994, 50, 5225.
13. For the syntheses of optically active 1, see: (a) Magnusson, G. Tetrahedron 1978, 34, 1385.
14. (b) Mori, K.; Tamada, S. Tetrahedron Lett. 1978 , 10, 901.
15. (c) Mori, K.; Tamada, S. Tetrahedron 1979, 35, 1279.
16. (d) Byström, S.; Högberg, H. E.; Norin, T. Tetrahedron 1981, 37, 2249.
17. (e) Kikukawa, T.; Imaida, M.; Tai, A. Bull. Chem. Soc. Jpn. 1984, 57, 1954.
18. (f) Itoh, T.; Yonekawa, Y.; Sato, T.; Fujisawa, T. Tetrahedron Lett. 1986, 27, 5405.
19. (g) Larchevêque, M.; Sanner, C. Tetrahedron 1988, 44, 640
20. (h) Reference 3a.
21. (i) Högberg, H. E.; Wassgren, A. B.; Hjalmarsson. M.; Bergström, G.; Löfqvist, J.; Norin, T. Tetrahedron 1990, 46, 3007.
22. (j) Huang, P.-Q.; Lan, H.-Q.; Zheng, X.; Ruan, Y.-P. J. Org. Chem. 2004, 69, 3964.
23. Wang, Z.-K.; Tian, W.-S.; Pan, X.-F. Acta Chim. Sinica 2007, 65, 705 (in Chinese).
24. Perrin, D. D.; Armarego, W. L. F.; Rerrin, D. R. Purification of Laboratory Chemicals, Pergamon Press, Oxford, 1980.
25. Cahiez, G.; Chaboche, C.; Jézéquel, M. Tetrahedron 2000, 56, 2733.