Model studies towards the synthesis of gilvocarcin M

Organic and Biomolecular Chemistry

Volumn 3, Issue 24, 2005, Pages 4432-4443

  Cordera Vargas, Alejandro ^a   Quiclet Sire, Béatrice ^a   Zard, Samir Z ^a  

^a LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCHEMISTRY; FREE RADICALS; SUGARS; SYNTHESIS (CHEMICAL);

AROMATIC RINGS; GILVOCARCIN M;

AROMATIC COMPOUNDS;

AMINOGLYCOSIDE; CYCLOALKANE DERIVATIVE; GILVOCARCIN M; LACTONE; LEAD;

ARTICLE; CATALYSIS; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; CLASSIFICATION; CYCLIZATION; SYNTHESIS;

AMINOGLYCOSIDES; CATALYSIS; CYCLIZATION; CYCLOPARAFFINS; LACTONES; LEAD; MODELS, CHEMICAL; MOLECULAR STRUCTURE;

EID: 29844439431     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b512851j     Document Type: Article

References (32)

1. For reviews see: (a) C. Jaramillo and S. Knapp, Synthesis, 1994, 1;
2. (b) K. Suzuki and T. Matsumoto, in Preparative Carbohydrate Chemistry, ed. S. Hanessian, Marcel-Dekker, New York, 1997, pp. 527-542;
3. (c) M. H. D. Posteme, Tetrahedron, 1992, 48, 8545A.
4. (a) T. Matsumoto, T. Hosya and K. Suzuki, J. Am. Chem. Soc., 1992, 114, 3568;
5. (b) T. Hosoya, E. Takashiro, T. Matsumoto and K. Suzuki, J. Am. Chem. Soc., 1994, 116, 1004.
6. (a) L. Kalvoda, J. Farkaa and F. Sorm, Tetrahedron Lett., 1970, 11, 2297;
7. (b) A. O. Stewart and R. M. Williams, J. Am. Chem. Soc., 1985, 107, 4289;
8. (c) O. R. Martin, S. P. Rao, K. G. Kurz and H. A. El-Shenawy, J. Am. Chem. Soc., 1988, 110, 8698;
9. (d) T. Matsumoto, M. Katsuki and K. Suzuki, Tetrahedron Lett., 1989, 30, 833;
10. (e) M. Yokoyama, H. Toyoshima, M. Shimizu, J. Mito and H. Togo, Synthesis, 1998, 409;
11. (f) M. D. Lewis, K. Cha and Y. Kishi, J. Am. Chem. Soc., 1982, 104, 4976;
12. (g) S. A. Babirad, Y. Wang and Y. Kishi, J. Org. Chem., 1987, 52, 1370;
13. (h) R. W. Friesen and C. F. Sturino, J. Org. Chem., 1990, 55, 2572.
14. (a) D. E. Kaelin, O. D. Lopez and S. F. Martin, J. Am. Chem. Soc., 2001, 123, 6937;
15. (b) M. Yamaguchi, A. Horiguchi, C. Ikeura and T. Minami, J. Chem. Soc., Chem. Commun., 1992, 434;
16. (c) Y. Yamamoto, T. Saigoku, T. Ohgai, H. Nishiyama and K. Itoh, Chem. Commun., 2004, 2702;
17. (d) S. R. Pulley and J. P. Carey, J. Org. Chem., 1998, 63, 5275.
18. T. Matsumoto, T. Hosoya and K. Suzuki, Tetrahedron Lett., 1990, 31, 4629.
19. A. Cordero-Vargas, B. Quiclet-Sire and S. Z. Zard, Tetrahedron Lett., 2004, 45, 7335.
20. P. P. Deshpande and O. R. Martin, Tetrahedron Lett., 1990, 31, 6313.
21. D. J. Hart and G. H. Merriman, Tetrahedron Lett., 1989, 30, 5093.
22. T. Kinoshita and T. Miwa, Carbohydr. Res., 1985, 143, 249.
23. Stereochemical assignements of compounds 19 and 20 were based on NOE data. On this basis, and knowing the cyclisation mechanisms, we established the absolute configuration of the open-chain glycoside 18 as R.
24. (a) S. Hanessian, J.-Y. Sancéau and P. Chemla, Tetrahedron, 1995, 51, 6669;
25. (b) W. Pitsch, A. Russel, M. Zabel and B. König, Tetrahedron, 2001, 57, 2345;
26. A. Dondoni, G. Mariotti and A. Marra, J. Org. Chem., 2002, 67, 4475.
27. K. Bock, I. Lundt and C. Petersen, Carbohydr. Res., 1979, 68, 313.
28. The stereochemistry at C-1 for compound 30 was not determined. However, it should be a by correlation with olefin 20 and the reaction mechanism.
29. J. Xie, F. Durrat and J.-M. Valéry, J. Org. Chem., 2003, 68, 7896.
30. (a) J. Barluenga, B. Pedregal and J. M. Concellón, Tetrahedron Lett., 1978, 307;
31. (b) I. Shiina, Y. Imai, M. Suzuki, M. Yanagisawa and T. Mukaiyama, Chem. Lett., 2000, 1062.
32. A. Cordero-Vargas, I. Pérez-Martin, B. Quiclet-Sire and S. Z. Zard, Org. Biomol. Chem., 2004, 2, 3018.