Concise synthesis of (4R,9Z)-octadec-9-en-4-olide, the female sex pheromone of Janus integer

European Journal of Organic Chemistry

Volumn , Issue 10, 2005, Pages 2040-2044

  Mori, Kenji ^a  

^a Fuji Flavor Co Ltd   (Japan)

Author keywords

Dihydroxylation; Epoxides; Lactones; Natural products; Pheromones

Indexed keywords

EID: 19844373517     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400830     Document Type: Article

References (13)

1. A. A. Cossé, R. J. Bartelt, D. G. James, R. J. Petroski, J. Chem. Ecol. 2001, 27, 1841-1851.
2. D. G. James, R. J. Petroski, A. A. Cossé, B. W. Zilkowski, R. J. Bartelt, J. Chem. Ecol. 2003, 29, 2189-2199.
3. C. Shibata, K. Mori, Eur. J. Org. Chem. 2004, 1083-1088.
4. H. C. Kolb, M. S. VanNieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2485-2547.
5. M. Tokunaga, J. F. Larrow, F. Kakiuchi, E. N. Jacobsen, Science 1997, 277, 936-938.
6. E. N. Jacobsen, Acc. Chem. Res. 2000, 33, 421-431.
7. J. A. Dale, H. S. Mosher, J. Am. Chem. Soc. 1973, 95, 512-519.
8. H. C. Kolb, K.B. Sharpless, Tetrahedron 1992, 48, 10515-10530.
9. Y. Aoyagi, Y. Saitoh, T. Ueno, M. Horiguchi, K. Takeya, R. M. Williams, J. Org. Chem. 2003, 68, 6899-6904.
10. T. Sugai, K. Mori, Agric. Biol. Chem. 1984, 48, 2497-2500.
11. K. Mori, in The Total Synthesis of Natural Products, vol. 9 (Ed.: J. ApSimon), John Wiley & Sons, New York, 1992, 216-273.
12. A. I. Meyers, E. D. Mihelich, R. L. Nolen, J. Org. Chem. 1974, 39, 2783-2787.
13. P. H. G. Zarbin, A. R. M. Oliveira, F. Simonelli, J. A. F. P. Villar, O. Delay, Jr., Tetrahedron Lett. 2004, 45, 7399-7400.