Synthetic studies towards picrasane quassinoids

Tetrahedron

Volumn 63, Issue 10, 2007, Pages 2335-2350

  Marcos, I S ^a   Garcia N ^a   Sexmero, M J ^a   Hernandez F A ^a   Escola, M A ^a   Basabe, P ^a   Diez D ^a   Urones, J G ^a  

^a UNIVERSITY OF SALAMANCA   (Spain)

Author keywords

ent Halimic acid; Picrasane; Quassinoids; Triterpenes

Indexed keywords

16 DIACETOXY 4,5 SECO 8 (18-14) ABEOPICRAS 7 EN 4 ONE; 16 DIACETOXY 4,5 SECO 8 (18-14) ABEOPICRAS 7 EN 4,6 DIONE; 16 TERT BUTYLDIMETHYLSILYLOXY 4 (2,2 DIMETHYLPROPYLENDIOXY) 4,5 SECO 8 (18-14) ABEOPICRAS 7 EN 1 OL; 1ALPHA,16 DIACETOXY 4BETA HYDROXY 8 (18-14) ABEO 5 EPIPICRAS 7 EN 6 ONE; 1ALPHA,16 DIACETOXY 8 (18-14) ABEO 5 EPIPICRASA 3,7 DIEN 6 ONE; 1ALPHA,16 DIACETOXY 8 (18-14) ABEO 5 EPIPICRASA 4(19),7 DIEN 6 ONE; 1ALPHA,6ALPHA,16 TRIACETOXY 8 (18-14) ABEO 5 EPIPICRAS 7 EN 4BETA OL; 1BETA ACETOXY 16 HYDROXY 8 (18-14) ABEO 5 EPIPICRASA 3,7 DIEN 6 ONE; 1BETA,16 DIACETOXY 4BETA HYDROXY 8 (18-14) ABEO 5 EPIPICRAS 7 EN 6 ONE; 1BETA,16 DIACETOXY 8 (18-14) ABEO 5 EPIPICRASA 3,7 DIEN 6 ONE; 1BETA,16 DIACETOXY 8 (18-14) ABEO 5 EPIPICRASA 4(19),7 DIEN 6 ONE; 4 [(2,2 DIMETHYL)PROPYLENDIOXY] 4,5 SECO 8 (18-14) ABEOPICRAS 7 EN 16 DIOL; 4 [(2,2 DIMETHYL)PROPYLENDIOXY] 4,5 SECO 8 (18-14) ABEOPICRAS 7 EN 16 DIOL DIACETATE; 8 (18-14) ABEO 5 EPIPICRAS 7 EN 1ALPHA,4BETA,6ALPHA,16 TETRAOL; 8 (18-14) ABEO 5 EPIPICRASA 1BETA,4BETA,6,16 TETRAOL; QUASSINOID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL;

EID: 33846626756     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.12.054     Document Type: Article

References (63)

1. Polonsky J. Fortschr. Chem. Org. Naturst. 30 (1973) 101
2. Polonsky J. Fortschr. Chem. Org. Naturst. 47 (1985) 211
3. San Fernando E.S., Gadek P.A., and Quinn C. Am. J. Bot. 82 (1995) 92
4. Polonsky J., Gallas J., Varenne J., Prangé T., Pascard C., Jacquemin H., and Moretti C. Tetrahedron Lett. (1982) 869
5. Wani M.C., Taylor H.L., Thompson J.B., and Wall M.E. J. Nat. Prod. 41 (1978) 578
6. Okano M., Fujita T., Fukamiya N., and Aratani T. Chem. Lett. (1984) 221
7. Shing T.K.M., Zhu X.Y., and Yeung Y.-Y. Chem.-Eur. J. 9 (2003) 5489
8. Shing T.K.M., and Yeung Y.-Y. Chem.-Eur. J. 12 (2006) 8367
9. Kim I.H., Suzuki R., Hitotsuyanagi Y., and Takeya K. Tetrahedron 59 (2003) 9985
10. Kupchan S.M., Britton R.W., Ziegler M.F., and Sigel C.W. J. Org. Chem. 38 (1973) 178
11. Kupchan S.M., Britton R.W., Lacadie J.A., Ziegler M.F., and Sigel C.W. J. Org. Chem. 40 (1975) 648
12. Phillipson J.D., and Darwish F.A. Planta Med. 41 (1981) 209
13. Cuendet M., and Pezzuto J.M. J. Nat. Prod. 67 (2004) 269
14. Hitotsuyanagi Y., Kim I.H., Hasuda T., Yamauchi Y., and Takeya K. Tetrahedron 62 (2006) 4262
15. Stojanac N., Sood A., Stojanac Z., and Valenta Z. Can. J. Chem. 53 (1975) 619
16. Stojanac N., Stojanac Z., White P.S., and Valenta Z. Can. J. Chem. 57 (1979) 3346
17. Kraus G.A., and Taschner M.J. J. Org. Chem. 45 (1980) 1175
18. Pfenninger J., and Graf W. Helv. Chim. Acta 63 (1980) 1562
19. Mandel L., Lee D.E., and Courtney L.F. J. Org. Chem. 47 (1982) 610
20. Voyle M., Dunlap N.K., Watt D.S., and Panderson O. J. Org. Chem. 48 (1983) 3242
21. Shishido K., Saitoh T., and Fukumoto R. J. Chem. Soc., Perkin Trans. 1 (1984) 2139
22. Koch H.J., Pfenninger H., and Graf W. Helv. Chim. Acta 58 (1975) 1727
23. Dias J.R., and Ramachandra R. J. Org. Chem. 42 (1977) 3584
24. Barrero A.F., Alvarez-Manzaneda E.J., Chahboun R., Cueva J.M., Aparicio M., and Romera J.L. Org. Lett. 3 (2001) 647
25. Alvarez-Manzaneda E.J., Romera J.L., Barrero A.F., Alvarez-Manzaneda R., Chahboun R., Meneses R., and Aparicio M. Tetrahedron 61 (2005) 837
26. Vidari G., Ferriño S., and Grieco P.A. J. Am. Chem. Soc. 106 (1984) 3539
27. Grieco P.A., Lis R., Ferriño S., and Jaw J.Y. J. Org. Chem. 49 (1984) 2342
28. Grieco P.A., Parker D.T., and Nargund R.P. J. Am. Chem. Soc. 110 (1988) 5568
29. Grieco P.A., Nargund R.P., and Parker D.T. J. Am. Chem. Soc. 111 (1989) 6287
30. Gross R.S., Grieco P.A., and Collins J.L. J. Am. Chem. Soc. 112 (1990) 9436
31. Fleck T.J., and Grieco P.A. Tetrahedron Lett. 33 (1992) 1813
32. Moher E.D., Collins J.L., and Grieco P.A. J. Am. Chem. Soc. 114 (1992) 2764
33. Grieco P.A., Collins J.L., Moher E.D., Fleck T.J., and Gross R.S. J. Am. Chem. Soc. 115 (1993) 6078
34. Moher E.D., Grieco P.A., and Collins J.L. J. Org. Chem. 58 (1993) 3789
35. Grieco P.A., and VanderRoest J.M. J. Am. Chem. Soc. 115 (1993) 5841
36. Grieco P.A., Cooke R.J., Henry K.J., and VanderRoest J.M. Tetrahedron Lett. 32 (1991) 4665
37. Marcos I.S., Sexmero M.J., Hernández F.A., Corrales M., Basabe P., Díez D., and Urones J.G. Molecules 11 (2006) 792
38. Marcos I.S., Pedrero A.B., Sexmero M.J., Díez D., Basabe P., Hernández F.A., and Urones J.G. Tetrahedron Lett. 44 (2003) 369
39. Marcos I.S., Pedrero A.B., Sexmero M.J., Díez D., García N., Escola M.A., Basabe P., Conde A., Moro R.F., and Urones J.G. Synthesis (2005) 3301
40. Marcos I.S., Hernández F.A., Sexmero M.J., Díez D., Basabe P., Pedrero A.B., García N., Sanz F., and Urones J.G. Tetrahedron Lett. 43 (2002) 1243
41. Marcos I.S., Hernández F.A., Sexmero M.J., Díez D., Basabe P., Pedrero A.B., García N., and Urones J.G. Tetrahedron 60 (2003) 685
42. Marcos I.S., Pedrero A.B., Sexmero M.J., Díez D., Basabe P., Hernández F.A., Broughton H.B., and Urones J.G. Synlett (2002) 105
43. Marcos I.S., Pedrero A.B., Sexmero M.J., Díez D., Basabe P., García N., Moro R.F., Broughton H.B., Mollinedo F., and Urones J.G. J. Org. Chem. 68 (2003) 7496
44. Marcos I.S., García N., Sexmero M.J., Basabe P., Díez D., and Urones J.G. Tetrahedron 61 (2005) 11672
45. Marcos I.S., Martínez B., Sexmero M.J., Díez D., Basabe P., and Urones J.G. Synthesis (2006) 3865
46. Qiao L., and Vederas J.C. J. Org. Chem. 58 (1993) 3480
47. Liu P.S. J. Org. Chem. 52 (1987) 4717
48. Demnitz F.W.J., Philippini C., and Raphael R.A. J. Org. Chem. 60 (1995) 5114
49. Cooper M.S., Heaney H., Newbold A., and Sanderson W. Synlett (1990) 533
50. Ley S.V., Norman J., Griffith W.P., and Marsden S.P. Synthesis (1994) 639
51. Jones D.W., and Marmon R.J. J. Chem. Soc., Perkin Trans. 1 (1993) 681
52. Tokoyama K., Sakata J., Kuwajima I., Shimizu M., Nakamura E., and Noyori R. J. Org. Chem. 43 (1983) 932
53. Greene T., and Wuts P.G.M. Protective Groups in Organic Synthesis. 3rd ed. (1999), Wiley, New York, NY p 127
54. Nicolaou K.C., Xu J.Y., Kim S., Pfefferkorn J., Ohshima T., Vourloumis D., and Hosokawa S. J. Am. Chem. Soc. 120 (1998) 8661
55. Jung M.E. Tetrahedron 32 (1976) 3
56. Brun E.M., Casades I., Gil S., Mestres R., and Parra M. Tetrahedron Lett. 39 (1998) 5443
57. Benesch L., Bury P., Guillaneux D., Houldsworth S., Wang X., and Snieckus V. Tetrahedron Lett. 39 (1998) 961
58. Domingo L.R., Gil S., Parra M., Sáez J.A., and Torres M. Tetrahedron 59 (2003) 6233
59. Marshall J.A., and Schaeffer D.J. J. Org. Chem. 30 (1965) 3642
60. Gawley R.E. Synthesis (1976) 777
61. Johnson W.S., Korst J.J., Clement R.A., and Dutta J. J. Am. Chem. Soc. 82 (1960) 614
62. Marino J.P., and Jaén J.C. J. Am. Chem. Soc. 104 (1982) 3165
63. Wasson R.L., and House H.O. Organic Synthesis Collect. Vol. IV (1963), Wiley, New York, NY p 552