Efficient formal synthesis of (±)-axamide-1 and (±)- axisonitrile-1 via an intramolecular Hosomi-Sakurai reaction

Tetrahedron Letters

Volumn 51, Issue 27, 2010, Pages 3542-3544

  Takahashi, Kazunori ^a   Takeda, Kentaro ^a   Honda, Toshio ^a  

^a HOSHI UNIVERSITY   (Japan)

Author keywords

Axamide 1; Axane sesquiterpene; Axisonitrile 1; Intramolecular Hosomi Sakurai reaction; Short step synthesis

Indexed keywords

AXAMIDE 1; AXISONITRILE 1; TERPENOID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DIHYDROXYLATION; INTRAMOLECULAR HOSOMI SAKURAI REACTION; SYNTHESIS;

EID: 77954243287     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.04.119     Document Type: Article

References (31)

1. F. Isolation Cafieri, E. Fattorusso, S. Magno, C. Santacroce, and E. Sica Tetrahedron 29 1973 4259 4262
2. E. Fattorusso, S. Magno, L. Mayol, C. Santacroce, and D. Sica Tetrahedron 30 1974 3911 3913
3. M. Adinolfi, L. De Napoli, B. Di Blasio, A. Iengo, C. Pedone, and C. Santacroce Tetrahedron Lett. 18 1977 2815 2816
4. A. Iengo, L. Mayol, and C. Santacroce Experentia 33 1977 11 12
5. A. Iengo, C. Santacroce, and G. Sodano Experentia 35 1979 10 11
6. G. Cimino, S. De Rosa, S. De Stefano, and G. Sodano Comp. Biochem. Physiol. 73B 1982 471 474
7. E. Fattorusso, S. Magno, L. Mayol, C. Santacroce, and D. Sica Tetrahedron 31 1975 269 270
8. J.R. Pawlik Chem. Rev. 93 1993 1911 1922
9. E. Piers, and B.W.A. Yeung Can. J. Chem. 64 1986 2475 2476
10. E. Piers, B.W.A. Yeung, and S.J. Rettig Tetrahedron 43 1987 5521 5535
11. A.-C. Guevel, and D.J. Hart Synlett 1994 169 170
12. D.J. Hart, and C.-S. Lai Synlett 1989 49 51
13. B. Chenera, C.-P. Chuang, D.J. Hart, and C.-S. Lai J. Org. Chem. 57 1992 2018 2029
14. A.-C. Guevel, and D.J. Hart J. Org. Chem. 61 1996 473 479
15. Y.-L. Kuo, M. Dhanasekaran, and C.-K. Sha J. Org. Chem. 74 2009 2033 2038
16. T. Ohkubo, H. Akino, M. Asaoka, and H. Takei Tetrahedron Lett. 36 1995 3365 3368
17. K. Takahashi, M. Watanabe, and T. Honda Angew. Chem., Int. Ed. 47 2008 131 133
18. K. Takahashi, R. Akao, and T. Honda J. Org. Chem. 74 2009 3424 3429
19. For recent reports on the Sakurai reaction, see: S.E. Denmark, B.R. Henke, and E. Weber J. Am. Chem. Soc. 109 1987 2512 2514
20. S. Hatakeyama, M. Kawamura, E. Shimanuki, K. Saijo, and S. Takano Synlett 1992 114 116
21. I.E. Markó, and D.J. Bayston Tetrahedron 50 1994 7141 7156
22. S.E. Denmark, and N.G. Almstead J. Org. Chem. 59 1994 5130 5132
23. M. Cordes Synthesis 2001 2470 2476
24. B. Leroy, and I.E. Markó J. Org. Chem. 67 2002 8744 8752
25. J. Pospisil, T. Kumamoto, and I.E. Markó Angew. Chem. 118 2006 3435 3438
26. Angew. Chem., Int. Ed. 118 2006 3357 3360
27. L. JimInéz-González, S. Garcia-Munoz, M. Alvarez-Corral, M. Munoz-Dorado, and I. Rodriguez-Garcia Chem. Eur. J. 13 2007 557 568
28. 28Si: 236.1960, found; 236.1970.
29. 18O+H: 167.1436, found; 167.1436.
30. S.E. Denmark, and J. Fu Chem. Rev. 103 2003 2763 2793
31. J.R. Parikh, and W.V.E. Doering J. Am. Chem. Soc. 84 1967 5505 5507