A xanthate-based free radical approach to defucogilvocarcin M

Tetrahedron Letters

Volumn 51, Issue 4, 2010, Pages 602-604

  Cortezano Arellano, Omar ^a   Cordero Vargas, Alejandro ^a  

^a UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

1 TETRALONE DERIVATIVE; AROMATIC COMPOUND; CHLORIDE; DEFUCOGILVOCARCIN M; ESTER DERIVATIVE; FREE RADICAL; GLYCOSIDE; NAPHTHALENE DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG; XANTHIC ACID DERIVATIVE;

ADDITION REACTION; AROMATIZATION; ARTICLE; CATALYSIS; CATALYST; CYCLIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 72149131176     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.11.076     Document Type: Article

References (36)

1. Takahashi K., Yoshida M., Tomita F., and Shirahata K. J. Antibiot. 34 (1981) 266
2. Misra R., Tritch III H.R., and Pandey R.C. J. Antibiot. 38 (1985) 1280
3. Tse-Dihn T.-C., and McGee L.R. Biochem. Biophys. Res. Commun. 143 (1987) 808
4. Liu T., Kharel M.K., Zhu L., Bright S.A., Mattingly C., Adams V.R., and Rohr J. ChemBioChem 10 (2009) 278
5. For reviews see:. Jaramillo C., and Knapp S. Synthesis (1994) 1
6. Suzuki K., and Matsumoto T. In: Hanessian S. (Ed). Preparative Carbohydrate Chemistry (1997), Marcel-Dekker, New York 527-542
7. Posteme M.H.D. Tetrahedron 48 (1992) 8545
8. Outten R.A., and Daves Jr. G.D. J. Org. Chem. 54 (1989) 29
9. Cordero-Vargas A., Quiclet-Sire B., and Zard S.Z. Org. Biomol. Chem. 3 (2005) 4432
10. Matsumoto T., Hosya T., and Suzuki K. J. Am. Chem. Soc. 114 (1992) 3568
11. Hosoya T., Takashiro E., Matsumoto T., and Suzuki K. J. Am. Chem. Soc. 116 (1994) 1004
12. McGee L.R., and Confalone P.N. J. Org. Chem. 53 (1988) 3695
13. Jung M.E., and Jung Y.H. Tetrahedron Lett. 29 (1988) 2517
14. Hart D.J., and Merriman G.H. Tetrahedron Lett. 30 (1989) 5093
15. McKenzie T.C., Hassen W., and McDonald S.J.F. Tetrahedron Lett. 28 (1987) 5435
16. McKenzie T.C., and Hassen W. Tetrahedron Lett. 28 (1987) 2563
17. McDonald S.J.F., McKenzie T.C., and Hassen W. J. Chem. Soc., Chem. Commun. (1987) 1528
18. Parker K.A., and Coburn C.A. J. Org. Chem. 56 (1991) 1666
19. James C.A., and Sniekus V. J. Org. Chem. 74 (2009) 4080
20. Takemura I., Imura K., Matsumoto T., and Suzuki K. Org. Lett. 6 (2004) 2503
21. Deshpande P.P., and Martin O.R. Tetrahedron Lett. 31 (1990) 6313
22. Cordero-Vargas A., Quiclet-Sire B., and Zard S.Z. Tetrahedron Lett. 45 (2004) 7335
23. For reviews on xanthates, see:. Zard S.Z. Angew. Chem., Int. Ed. 36 (1997) 672
24. Zard S.Z. In: Renaud P., and Sibi M. (Eds). Radicals in Organic Synthesis (2001), Wiley-VCH, Weinheim 90-108
25. Liard A., Quiclet-Sire B., Saicic R., and Zard S.Z. Tetrahedron Lett. 38 (1997) 1759
26. Cordero-Vargas A., Quiclet-Sire B., and Zard S.Z. Org. Lett. 5 (2003) 3717
27. 2: 27% yield).
28. Iodine derivative was prepared by reaction of known 2'-benzyloxy-2-bromoacetophenone with NaI in acetone. For the preparation of the bromo derivative, see:. Black M., Cadogan J.I.G., McNab H., MacPherson A.D., Roddam V.P., Smith C., and Swenson H.R. J. Chem. Soc., Perkin Trans. 1 (1997) 2483
29. Ollivier C., Bark T., and Renaud P. Synthesis (2000) 1598
30. 2 system was also applied unsuccessfully to this reaction. For triethylborane-mediated radical reactions, see:. Yorimitsu H., and Oshima K. In: Renaud P., and Sibi M. (Eds). Radicals in Organic Synthesis (2001), Wiley-VCH, Weinheim 11-27
31. 3B, α-carbonyl radicals could evolve the corresponding boron enolates. This is probably the reason why nothing but reduction product in the attempted radical addition of 9b to vinyl pivalate was observed. For examples on boron enolates, see:. Nozaki K., Oshima K., and Utimoto K. Tetrahedron Lett. 29 (1988) 1041
32. Beraud V., Gnanou J.C., Walton B., and Maillard B. Tetrahedron Lett. 41 (2000) 1195
33. Cordero-Vargas A., Pérez-Martín I., Quiclet-Sire B., and Zard S.Z. Org. Biomol. Chem. 2 (2004) 3018
34. When we forced the bromination reaction to completion by adding extra amounts of NBS, the starting material disappeared completely, but a number of by-products were formed and the global yields (after treatment with DBU) were considerably lower (40-50%). So, we decided to keep the amount of NBS at 1.1 equiv and to recycle the unreacted starting material.
35. Srikrishna A., and Ravikumar P.C. Synthesis (2007) 65
36. Liu W., Buck M., Chen N., Shang M., Taylor N.J., Asoud J., Wu X., Hasinoff B.B., and Dmitrenko G.I. Org. Lett. 9 (2007) 2915