Enantioselective synthesis of (1S,3S,7R)-3-methyl-α-himachalene, the sex pheromone of the sandfly Lutzomyia longipalpis from Jacobina, Brazil

Tetrahedron Letters

Volumn 41, Issue 27, 2000, Pages 5243-5247

  Mori, Kenji ^a   Tashiro, Takuya ^a   Sano, Satoshi ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Asymmetric synthesis; Circular dichroism; Diels Alder reaction; Pheromones; Terpenes and terpenoids

Indexed keywords

PHEROMONE; SEX PHEROMONE; TERPENE DERIVATIVE; TERPENOID DERIVATIVE;

ARTICLE; BRAZIL; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CIRCULAR DICHROISM; ENANTIOMER; METHYLATION; NONHUMAN; PSYCHODIDAE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

ARACHNIDA; BETULACEAE; HEXAPODA; LUTZOMYIA LONGIPALPIS; PSYCHODIDAE;

EID: 0034235917     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00831-5     Document Type: Article

References (22)

1. Ward, R. D. Adv. Disease Vector Res. 1989, 6, 91-126.
2. Hamilton, J. G. C.; Hooper, A. M.; Ibbotson, H. C.; Kurosawa, S.; Mori, K.; Muto, S.; Pickett, J. A. Chem. Commun. 1999, 2335-2336.
3. Muto, S.; Nishimura, Y.; Mori, K. Eur. J. Org. Chem. 2000, 2159-2165.
4. Kurosawa, S.; Mori, K. Eur. J. Org. Chem. 2000, 955-962.
5. Hamilton, J. G. C.; Hooper, A. M.; Mori, K.; Pickett, J. A.; Sano, S. Chem. Commun. 1999, 355-356.
6. Sano, S.; Mori, K. Eur. J. Org. Chem. 1999, 1679-1686.
7. Joseph, T. C.; Dev, S. Tetrahedron 1968, 24, 3841-3852.
8. Pickett, J. A. et al. Chem. Commun., in preparation.
9. Joseph, T. C.; Dev, S. Tetrahedron 1968, 24, 3809-3827.
10. Crabbé, P. Optical Rotatory Dispersion and Circular Dichroism in Organic Chemistry; Holden-Day: San Francisco, 1965; pp. 72-157.
11. Youn, J. K.; Yon, G. H.; Pak, C. S. Tetrahedron Lett. 1986, 27, 2409-2410.
12. Evans, D. A.; Gaze, J. R.; Leighton, J. L. J. Am. Chem. Soc. 1992, 114, 9434-9453.
13. Evans, D. A.; Ennis, M. D.; Mathre, D. J. J. Am. Chem. Soc. 1982, 104, 1737-1739.
14. Gaze, J. R.; Evans, D. A. Org. Synth. Coll. Vol. 1993, 8, 339-343.
15. Oppolzer, W.; Blagg, J.; Rodriguez, I.; Walther, E. J. Am. Chem. Soc. 1980, 112, 2767-2772.
16. Oppolzer, W.; Moretti, R.; Thomi, S. Tetrahedron Lett. 1989, 30, 5603-5606.
17. Nakamura, Y.; Mori, K. Biosci., Biotechnol., Biochem., in press.
18. Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815-3818.
19. Grieco, P. A.; Handy, S. T.; Beck, J. P. Tetrahedron Lett. 1994, 35, 2663-2666.
20. Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. J. Am. Chem. Soc. 1978, 100, 3611-3613.
21. Pine, S. H. Org. Reactions 1993, 43, 1-91.
22. In Refs. 2, 3, 5 and 6, (1S,3S,7R)-1 was erroneously described as (1S,3S,7S)-1. We thank a referee for his kind correction.