Pure Appl. Chem., 2007, Vol. 79, No. 4, pp. 491-505
http://dx.doi.org/10.1351/pac200779040491
Recent heterocyclic compounds from marine invertebrates: Structure and synthesis
References
- 1. D. J. Faulkner. Nat. Prod. Rep. 20, 1 (2003) and earlier reports in this series.
- 2. J. W. Blunt, B. R. Copp, M. H. G. Munro, P. T. Northcote, M. R. Prinsep. Nat. Prod. Rep. 22, 15 (2005) and earlier reports in the series.
- 3. M. H. G. Munro, J. W. Blunt. Marine Literature Database, Dept. of Chemistry, University of Canterbury, New Zealand (2006).
- 4. Y. Kashman, S. Hirsch, O. J. McConnell, I. Ohtani, T. Kusumi. J. Am. Chem. Soc. 111, 8925 (1989). (http://dx.doi.org/10.1021/ja00206a029)
- 5. I. Spector, N. R. Shochet, Y. Kashman, A. Groweiss. Science 219, 493 (1983). (http://dx.doi.org/10.1126/science.6681676)
- 6. A. Rudi, Y. Kashman. J. Org. Chem. 54, 5331 (1989). (http://dx.doi.org/10.1021/jo00283a029)
- 7. S. Carmely, M. Cojocaru, Y. Loya, Y. Kashman. J. Org. Chem. 53, 4801 (1988) and refs. therein.
- 8. P. R. Berquist, B. F. Bowden, R. C. Cambie, P. A. Craw, P. Karuso, A. Poiner, W. C. Taylor. Aust. J. Chem. 46, 623 (1993). (http://dx.doi.org/10.1071/CH9930623)
- 9. W. C. Taylor, S. Toth. Aust. J. Chem. 50, 895 (1997). (http://dx.doi.org/10.1071/C96166)
- 10. A. Rudi, Y. Erez, Y. Benayahu, Y. Kashman. Tetrahedron Lett. 46, 8613 (2005). (http://dx.doi.org/10.1016/j.tetlet.2005.09.047)
- 11. A. Rudi, G. Shmul, Y. Benayahu, Y. Kashman. Tetrahedron Lett. 47, 2937 (2006) and refs. therein.
- 12. C. C. Lin, H. J. Wu. Synthesis 6, 715 (1996). (http://dx.doi.org/10.1055/s-1996-4291)
- 13. L. Chill, A. Rudi, Y. Benayahu, M. Schleyer, Y. Kashman. Org. Lett. 6, 755 (2004). (http://dx.doi.org/10.1021/ol036454t)
- 14. A. Groweiss, Y. Kashman. Tetrahedron 39, 3385 (1983). (http://dx.doi.org/10.1016/S0040-4020(01)91590-X)
- 15. A. Rudi, Y. Benayahu, Y. Kashman. Org. Lett. 6, 4013 (2004). (http://dx.doi.org/10.1021/ol048358d)
- 16. S. Hirsch, A. Rudi, Y. Kashman. J. Nat. Prod. 54, 92 (1991). (http://dx.doi.org/10.1021/np50073a005)
- 17. S. Loya, R. Tal, Y. Kashman, A. Hizi. Antimicrob. Agents Chemother. 34, 2009 (1990).
- 18. L. Chill, M. Aknin, Y. Kashman. Org. Lett. 5, 2433 (2003). (http://dx.doi.org/10.1021/ol034615n)
- 19. G. R. Pettit, R. Tan, J. Xu, Y. Ichihara, M. D. Williams, M. R. Boyd. J. Nat. Prod. 61, 955 (1998). (http://dx.doi.org/10.1021/np9800405)
- 20. S. Fukuzawa, S. Matsunaga, N. Fusetani. J. Org. Chem. 62, 4484 (1997). (http://dx.doi.org/10.1021/jo970091r)
- 21. N. Imamura, M. Nishijima, T. Takadera, K. Adachi, M. Sakai, H. Sano. J. Antibiot. 50, 8 (1997).
- 22. D. Uemura, Y. Toya, I. Watanabe, Y. Hirata. Chem. Lett. 12, 1481 (1979). (http://dx.doi.org/10.1246/cl.1979.1481)
- 23. K. Watanabe, K. Iguchi, K. Fujimori. Heterocycles 49, 269 (1998).
- 24. R. Duran, E. Zubia, M. J. Ortega, S. Naranjo, J. Salva. Tetrahedron 55, 13225 (1999). (http://dx.doi.org/10.1016/S0040-4020(99)00803-0)
- 25. L. Chill, A. Rudi, Y. Benayahu, Y. Kashman. Tetrahedron Lett. 45, 7925 (2004). (http://dx.doi.org/10.1016/j.tetlet.2004.08.137)
- 26. B. R. Copp, J. Jompa, A. Tahir, C. M. Ireland. J. Org. Chem. 63, 8024 (1998). (http://dx.doi.org/10.1021/jo980905j)
- 27. G. Koren-Goldshlager, M. Aknin, E. M. Gaydon, Y. Kashman. J. Org. Chem. 63, 4601 (1998). (http://dx.doi.org/10.1021/jo9721453)
- 28. S. Kohmoto, O. J. McConnell, A. Wright. Experientia 44, 85 (1988). (http://dx.doi.org/10.1007/BF01960259)
- 29. P. Di Donato, A. Napolitano, G. Prota. Biochim. Biophys. Acta 1571, 157 (2002).
- 30. A. C. Stierle, J. H. Cardellina II, F. L. Singleton. Tetrahedron Lett. 32, 4827 (1991). (http://dx.doi.org/10.1016/S0040-4039(00)93476-2)
- 31. H. Susuki, K. Shindo, A. Ueno, T. Miura, M. Takei, M. Sakakibara, H. Fukamachi, J. Tanaka, T.Higa. Bioorg. Med. Chem. Lett. 9, 1361 (1999). (http://dx.doi.org/10.1016/S0960-894X(99)00205-X)
- 32. C. D. J. Boden, G. J. Pattenden. J. Chem. Soc., Perkin Trans. 1 875 (2000). (http://dx.doi.org/10.1039/a909360e)
- 33. X. Fu, J. Su, L. Xeng. Sci. China, Ser. B 43, 643 (2000).
- 34. H. Vervoot, W. Fenical, R. Epitanio. J. Org. Chem. 65, 782 (2000). (http://dx.doi.org/10.1021/jo991425a)
- 35. A. Rudi, L. Chill, M. Aknin, Y. Kashman. J. Nat. Prod. 66, 575 (2003). (http://dx.doi.org/10.1021/np020531w)
- 36. A. Rudi, M. Aknin, E. M. Gaydou, Y. Kashman. Tetrahedron 54, 13203 (1998). (http://dx.doi.org/10.1016/S0040-4020(98)00801-1)
- 37. P. Marfey. Carlsberg Res. Commun. 49, 591 (1984).
- 38. T. Evan, A. Rudi, M. Ilan, Y. Kashman. J. Nat. Prod. 64, 226 (2001). (http://dx.doi.org/10.1021/np000383e)
- 39. H. Sorek, A. Rudi, M. Aknin, E. Gaydou, Y. Kashman. Tetrahedron Lett. 47, 7237 (2006). (http://dx.doi.org/10.1016/j.tetlet.2006.07.128)
- 40. A. Rudi, I. Goldberg, Z. Stein, F. Frolow, Y. Benayahu, M. Schleyer, Y. Kashman. J. Org. Chem. 59, 999 (1994). (http://dx.doi.org/10.1021/jo00084a015)
- 41. A. Rudi, T. Evan, M. Aknin, Y. Kashman. J. Nat. Prod. 63, 832 (2000). (http://dx.doi.org/10.1021/np9905158)
- 42. R. A. Andersen, D. J. Faulkner, H. Cun-Heng, G. D. Van Duyne, J. Clardy. J. Am. Chem. Soc. 107, 5492 (1985). (http://dx.doi.org/10.1021/ja00305a027)
- 43. W. Y. Voshida, K. K. Lee, A. R. Carroll, P. J. Scheuer. Helv. Chem. Acta 75, 1721 (1992). (http://dx.doi.org/10.1002/hlca.19920750525)
- 44. A. Terpin, K. Polborn, W. Steglich. Tetrahedron 51, 9941 (1995). (http://dx.doi.org/10.1016/0040-4020(95)00568-S)
- 45. S. Loya, A. Rudi, Y. Kashman, A. Hizi. Biochem. J. 344, 85 (1999). (http://dx.doi.org/10.1042/0264-6021:3440085)
- 46. G. Koren-Goldshlager, Y. Kashman, M. Schleyer. Nat. Prod. 61, 282 (1998). (http://dx.doi.org/10.1021/np970442x)
- 47. Y. Kashman, G. Koren-Goldshlager, M. D. Garcia Gravalos, M. Schleyer. Tetrahedron Lett. 40, 997 (1999). (http://dx.doi.org/10.1016/S0040-4039(98)02467-8)
- 48. M. R. Heinrich, Y. Kashman, P. Spiteller, W. Steglich. Tetrahedron 57, 9973 (2001). (http://dx.doi.org/10.1016/S0040-4020(01)01020-1)
- 49. R. Sakai, S. Komoto, T. Higa, C. W. Jefford, C. Bernardinelli. Tetrahedron Lett. 28, 5493 (1987). (http://dx.doi.org/10.1016/S0040-4039(00)96762-5)
- 50. R. M. Markus, W. Steglich, M. G. Bannel, Y. Kashman. Tetrahedron 59, 9239 (2003). (http://dx.doi.org/10.1016/j.tet.2003.02.005)
- 51. J. C. Braekman, D. Daloze, R. Tarares, E. Hajdu, R. W. M. Van Soest. J. Nat. Prod. 63, 193 (2000) and refs. therein.
- 52. A. D. Patil, N. V. Kumar, W. C. Kokke, M. F. Bean, A. J. Freyer, C. De Brosse, S. Mai, A. Truneh, B. Carte, A. L. Breen, R. P. Hertzberg, R. K. Johnson, J. W. Westley, B. C. M. Potts. J. Org. Chem. 60, 1182 (1995). (http://dx.doi.org/10.1021/jo00110a021)
- 53. A. D. Patil, A. J. Freyer, P. B. Taylor, B. Carte, G. Zuber, R. K. Johnson, D. J. Faulkner. J. Org. Chem. 62, 1814 (1997). (http://dx.doi.org/10.1021/jo962084t)
- 54. E. Polagiano, S. Demarino, L. Minale, R. Riccio, F. Zollo, M. Iorizzi, J. B. Carte, C. Debitus, L.Lucarain, J. Provost. Tetrahedron 51, 3675 (1995). (http://dx.doi.org/10.1016/0040-4020(95)00082-J)
- 55. H. Sorek, A. Rudi, S. Gueta, F. Reyes, M. Jesus Martin, M. Aknin, E. Gaydou, J. Vacelet, Y.Kashman. Tetrahedron 62, 8838 (2006). (http://dx.doi.org/10.1016/j.tet.2006.06.063)
- 56. T. Yosief, A. Rudi, Y. Kashman. J. Nat. Prod. 63, 229 (2000). (http://dx.doi.org/10.1021/np9902690)
- 57. A. Rudi, M. Aknin, E. Gaydou, Y. Kashman. J. Nat. Prod. 67, 1932 (2004). (http://dx.doi.org/10.1021/np049834b)
- 58. A. Rudi, Y. Kashman. J. Nat. Prod. 55, 1408 (1992). (http://dx.doi.org/10.1021/np50088a004)
- 59. D. Pappo, A. Rudi, Y. Kashman. Tetrahedron Lett. 42, 5941 (2001). (http://dx.doi.org/10.1016/S0040-4039(01)01111-X)
- 60. D. Pappo, Y. Kashman. Tetrahedron 59, 6493 (2003). (http://dx.doi.org/10.1016/S0040-4020(03)01058-5)
- 61. D. Pappo, S. Shimony, Y. Kashman. J. Org. Chem. 70, 199 (2005). (http://dx.doi.org/10.1021/jo048622g)
- 62. N. Fusetani, S. Matsunaga. Curr. Org. Chem. 7, 945 (2003). (http://dx.doi.org/10.2174/1385272033486648)
- 63. N. Berer, A. Rudi, I. Goldberg, Y. Benayahu, Y. Kashman. Org. Lett. 6, 2543 (2004). (http://dx.doi.org/10.1021/ol0491787)
- 64. D. Pappo, M. Vartanian, S. Lang, Y. Kashman. J. Am. Chem. Soc. 127, 7682 (2005). (http://dx.doi.org/10.1021/ja050299r)
- 65. T. Nakazawa, T. Suzuki, M. Ishii. Tetrahedron Lett. 38, 8951 (1997). (http://dx.doi.org/10.1016/S0040-4039(97)10360-4)
- 66. D. Pappo, Y. Kashman. Org. Lett. 8, 1177 (2006). (http://dx.doi.org/10.1021/ol060075t)