Total synthesis of (±)-cyclooroidin

Tetrahedron Letters

Volumn 46, Issue 50, 2005, Pages 8635-8638

  Papeo, Gianluca ^a   Frau, María Antonia Gómez Zurita ^a,b   Borghi, Daniela ^a   Varasi, Mario ^a  

^a Nerviano Medical Sciences ^*  (Italy)

^b Centro de Investigación Biomolecular Aplicada CIBASA   (Spain)

Author keywords

Cyclooroidin; Pyrrole imidazole alkaloids; Wolff bromoketone synthesis

Indexed keywords

ALKALOID; CYCLOOROIDIN; IMIDAZOLE DERIVATIVE; LONGAMIDE B; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

AGELAS OROIDES; ARTICLE; DRUG ISOLATION; DRUG PURITY; DRUG SYNTHESIS; OPTICAL ROTATION; SPONGE (PORIFERA); WOLFF REARRANGEMENT;

AGELAS OROIDES; PORIFERA;

EID: 27744605691     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.10.060     Document Type: Article

References (31)

1. See, for example: J.W. Blunt, B.R. Copp, M.H.G. Munro, P.T. Northcote, and M.R. Prinsep Nat. Prod. Rep. 22 2005 15 61
2. B. Haefner Drug Discovery Today 8 2003 536 544
3. D.J. Newman, and G.N. Cragg J. Nat. Prod. 67 2004 1216 1238
4. H. Hoffmann, and T. Lindel Synthesis 12 2003 1753 1783
5. Z. Jin Nat. Prod. Rep. 22 2005 196 229
6. P. Andrade, R. Willoughby, S.A. Pomponi, and R.G. Kerr Tetrahedron Lett. 40 1999 4775 4778
7. T. Lindel, H. Hoffmann, M. Hochgürtel, and J.R. Pawlik J. Chem. Ecol. 26 2000 1477 1496
8. A. Al Mourabit, and P. Potier Eur. J. Org. Chem. 2001 237 243
9. R.G. Linington, D.E. Williams, A. Tahir, R. van Soest, and R.J. Andersen Org. Lett. 5 2003 2735 2738
10. N. Travert, and A. Al Mourabit J. Am. Chem. Soc. 126 2004 10252 10253
11. E. Fattorusso, and O. Taglialatela-Scafati Tetrahedron Lett. 41 2000 9917 9922
12. A. Umeyama, S. Ito, E. Yuasa, S. Arihara, and T. Yamada J. Nat. Prod. 61 1998 1433 1434
13. For similar approaches, see: T.L. Little, and S.E. Weber J. Org. Chem. 59 1994 7299 7305
14. V.B. Birman, and X.-T. Jiang Org. Lett. 6 2004 2369 2371
15. M.G. Banwell, A.M. Bray, A.C. Willis, and D.J. Wong New J. Chem. 23 1999 687 690
16. While this manuscript was under review, a paper dealing with the synthesis of optically pure (S)-enantiomers of hanishin, longamide B and longamide B methyl ester has been released: J. Patel, N. Pelloux-Léon, F. Minassian, and Y. Vallée J. Org. Chem. 70 2005 9081 9084
17. L. Wolff, and R. Greulich Ber. Dtsch. Chem. Ges. 45 1912 23
18. D.M. Bailey, and R.E. Johnson J. Med. Chem. 16 1973 1300 1302
19. S. Marchais, A. Al Mourabit, A. Ahond, C. Poupat, and P. Potier Tetrahedron Lett. 40 1999 5519 5522
20. A.C. Barrios Sosa, K. Yakushijin, and D.A. Horne Tetrahedron Lett. 41 2000 4295 4299
21. D.A. Evans, G. Borg, and K.A. Scheit Angew. Chem., Int. Ed. 41 2002 3188 3191
22. F. Cafieri, E. Fattorusso, A. Mangoni, and O. Taglialatela-Scafati Tetrahedron Lett. 36 1995 7893 7896
23. D.E.N. Jacquot, P. Mayer, and T. Lindel Chem. Eur. J. 10 2004 1141 1148
24. +.
25. T. Ye, and M.A. McKervey Chem. Rev. 94 1994 1091 1160
26. T. Aoyama, and T. Shioiri Chem. Pharm. Bull. 29 1981 3249 3255
27. 6): 36.2, 40.0, 41.8, 48.8, 99.5, 105.9, 114.1, 125.8, 157.3, 198.9.
28. C.W. Zapf, C.J. Creighton, M. Tomioka, and M. Goodman Org. Lett. 3 2001 1133 1136
29. R. Abou-Jneid, S. Ghoulami, M.-T. Martin, E. Tran Huu Dau, N. Travert, and A. Al Mourabit Org. Lett. 6 2004 3933 3936
30. 6): 58.9, 94.7, 158.8, 171.0, 213.0.
31. 3OD): 30.1, 43.4, 55.0, 108.7, 112.2, 117.3, 125.6, 128.3, 150.6, 161.4.