An efficient total synthesis of the anticancer agent (+)-spisulosine (ES-285) from Garner's aldehyde

Tetrahedron Letters

Volumn 51, Issue 31, 2010, Pages 4140-4142

  Ghosal, Partha ^a   Shaw, Arun K ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; ALKENE; ALLYL COMPOUND; AMINOALCOHOL; ANTINEOPLASTIC AGENT; GRIGNARD REAGENT; HYDROCARBON; NATURAL PRODUCT; SPISULOSINE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; DRUG SYNTHESIS; HYDROGENATION; HYDROLYSIS; STEREOCHEMISTRY;

EID: 77953961099     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.05.146     Document Type: Article

References (25)

1. Newman D.J., and Cragg G.M. J. Nat. Prod. 70 (2007) 461-477
2. Peterson Q.P., Hsu D.C., Goode D.R., Novotny C.J., Totten R.K., and Hergenrother P.J. J. Med. Chem. 52 (2009) 5721-5731
3. Jemal A., Siegel R., Ward E., Hao Y., Xu J., and Thun M.J.C.A. Cancer J. Clin. 59 (2009) 225-249
4. Dong Y., Shi Q., Pai H.-C., Peng C.-Y., Pan S.-L., Teng C.-M., Nakagawa-Goto K., Yu D., Liu Y.-N., Wu P.-C., Bastow K.-F., Morris-Natschke S.L., Brossi A., Lang J.-Y., Hsu J.L., Hung M.-C., Lee E.-Y.-H.P., and Lee K.-H. J. Med. Chem. 53 (2010) 2299-2308
5. Rinehart, K. L.; Fregeau, N. L.; Warwick, R. A.; Garcia Gravalos, D.; Avila, J.; Faircloth, G. T. WO 9952521A, 1999; Chem. Abstr. 1999, 131, 295576.
6. Acena, J. L.; Adrio, J.; Cuevas, C.; Gallego, P.; Manzanares, I.; Munt, S.; Rodriguez, I. WO 0194357 A1, 2001; Chem. Abstr. 2001, 136, 19976.
7. Cuadros R., Montejo de Garcini E., Wandosell F., Faircloth G., Fernández-Sousa J.M., and Avila J. Cancer Lett. 152 (2000) 23-29
8. Faircloth G., and Cuevas C. Progress in Molecular and Subcellular Biology Vol. 43 (2006), Springer, Berlin pp 363-379
9. Acena, J. L.; Adrio, J.; Cuevas, C.; Gallego, P.; Manzanares, I.; Munt, S.; Rodriguez, I. US Patent 2004/048834, 2004.
10. Yun J.M., Sim T.B., Hahm H.S., Lee W.K., and Ha H.-J. J. Org. Chem. 68 (2003) 7675-7680
11. Allepuz A.C., Badorrey R., Dìaz-de-Villegas M.D., and Gálvez J.A. Eur. J. Org. Chem. (2009) 6172-6178
12. Séguin C., Ferreira F., Botuha C., Chemla F., and Pérez-Luna A. J. Org. Chem. 74 (2009) 6986-6992
13. Amarante G.W., Cavallaro M., and Coelho F. Tetrahedron Lett. 51 (2010) 2597-2599
14. Ghosal P., Kumar V., and Shaw A.K. Carbohydr. Res. 345 (2010) 41-44
15. Kumar V., and Shaw A.K. J. Org. Chem. 73 (2008) 7526-7531
16. Reddy L.V.R., Swamy G.N., and Shaw A.K. Tetrahedron: Asymmetry 19 (2008) 1372-1375
17. Reddy L.V.R., Reddy P.V., and Shaw A.K. Tetrahedron: Asymmetry 18 (2007) 542-546
18. Garner P. Tetrahedron Lett. 25 (1984) 5855-5858
19. Srivastava A.K., Das S.K., and Panda G. Tetrahedron 65 (2009) 5322-5327
20. Srivastava A.K., and Panda G. Chem. Eur. J. 14 (2008) 4675-4688
21. Jackson M.D., Gould S.J., and Zabriskie T.M. J. Org. Chem. 67 (2002) 2934-2941
22. Savile C.K., Fabriàs G., and Buist P.H. J. Am. Chem. Soc. 123 (2001) 4382-4385
23. 4 reduction.
24. 3)}.
25. 1 286.3110, found 286.3119.