Ready access to the 6,8-dioxabicyclo[3.2.1]octane ring system using asymmetric heterocycloaddition induced by a chiral sulfoxide: Application to the total synthesis of the Mus musculus pheromone

Tetrahedron Asymmetry

Volumn 10, Issue 6, 1999, Pages 1041-1050

  Hayes, Patricia ^a   Maignan, Christian ^a  

^a UNIVERSITÉ DU MAINE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

OCTANE; PHEROMONE; SULFOXIDE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033605535     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00070-1     Document Type: Article

References (24)

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2. Aversa, M. C.; Barattocci, A.; Bonaccorsi, P.; Giannetto, P. Tetrahedron: Asymmetry 1997, 8, 1339.
3. Gosselin, P.; Bonfand, E.; Hayes, P.; Retoux, R.; Maignan, C. Tetrahedron: Asymmetry 1994, 5, 781.
4. Hayes, P.; Maignan, C. Synlett 1994, 409-410.
5. Hayes, P.; Dujardin, G.; Maignan, C. Tetrahedron Lett. 1996, 37, 3687.
6. Hayes, P.; Maignan, C. Synthesis 1998, in press.
7. Mori, K. In The Total Synthesis of Natural Products; Apsimon, J., Ed. John Wiley: New York, 1992; pp. 9, 381.
8. Wiesler, D. P.; Schwende, F. J.; Carmach, M.; Novotny, M. J. Org. Chem. 1984, 49, 882.
9. Ronan, B.; Kagan, H. B. Tetrahedron: Asymmetry 1992, 3, 115.
10. Bonfand, E.; Gosselin, P.; Maignan, C. Tetrahedron: Asymmetry 1993, 4, 1667.
11. Alexandre, C.; Rouessac, F.; Tabti, B. Tetrahedron Lett. 1985, 26, 5453.
12. The absolute configuration of crystalline (Ss)-9 was assigned to be (Ss,R)-9 on the basis of X-ray crystallography: Hayes, P.; Maignan, C., unpublished results.
13. Denis, J. N.; Krief, A. Tetrahedron Lett. 1979, 20, 3995.
14. Nakumura, K.; Kitayama, T.; Inoue, Y.; Ohno, A. Tetrahedron 1990, 46, 7471.
15. 2 or ortho-phenylene phosphorochloroditite without protection of the hydroxy group led, unexpectedly, to 3-p-tolylsulfanylpentan-3-one being the major/or single product.
16. Furukawa, N.; Fujihara, H. In The Chemistry of Sulfones and Sulfoxides; Pataï, S.; Rappoport, Z.; Stirling, C., Eds. Wiley: Chichester, 1988; p. 541.
17. For exo-brevicomin, see Kotsuki, H.; Kadota, I.; Ochi, M. J. Org. Chem. 1990, 55, 4417.
18. For endo-brevicomin, see Mori, K.; Seu, Y. B. Tetrahedron 1985, 41, 3429.
19. Eliel, E. L.; Doyle, T. W. J. Org. Chem. 1970, 35, 2716.
20. 3SnH system.
21. Three groups have reported asymmetric syntheses of the Mus musculus pheromone: (a) Mori, K.; Young-Bae, S. Tetrahedron 1986, 42, 5901.
22. (b) Wasserman, H. H.; Wolff, S.; Oku, T. Tetrahedron Lett. 1986, 27, 4909.
23. (c) Masaki, Y.; Ikuhiro, I.; Toshihiro, I.; Hirihisa, O.; Hiromu, N. Chem. Pharm. Bull. 1988, 36, 1241.
24. Nicolaou, K. C.; Seitz, S. P.; Sipio, W. J.; Blount, J. F. J. Am. Chem. Soc. 1979, 101, 3884.