Total syntheses and synthetic studies of spongiane diterpenes

Tetrahedron

Volumn 64, Issue 3, 2008, Pages 445-467

  González, Miguel A ^a  

^a UNIVERSITY OF VALENCIA   (Spain)

Author keywords

Diterpenes; Marine natural products; Spongiane; Synthesis

Indexed keywords

DITERPENE; DITERPENOID; SPONGIANE DITERPENOID; UNCLASSIFIED DRUG;

AROMATIZATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; ENANTIOSELECTIVITY; HYDROGENATION; ISOMERIZATION; LACTONIZATION; PRIORITY JOURNAL; REACTION ANALYSIS; REVIEW; SPONGE (PORIFERA); STRUCTURE ANALYSIS; SYNTHESIS;

EID: 36649034674     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.10.057     Document Type: Review

References (88)

1. Connolly J.D., and Hill R.A. Dictionary of Terpenoids Vol. 2 (1991), Chapman and Hall, London pp 895-899
2. Hanson J.R. Nat. Prod. Rep. 23 (2006) 875-885 and former reviews in this series
3. Faulkner D.J. Nat. Prod. Rep. 19 (2002) 1-49 and former reviews in this series
4. Faulkner D.J., Newman D.J., and Cragg G.M. Nat. Prod. Rep. 21 (2004) 50-76
5. Blunt J.W., Copp B.R., Munro M.H.G., Northcote P.T., and Prinsep M.R. Nat. Prod. Rep. 22 (2005) 15-61
6. Blunt J.W., Copp B.R., Munro M.H.G., Northcote P.T., and Prinsep M.R. Nat. Prod. Rep. 23 (2006) 26-78
7. Blunt J.W., Copp B.R., Hu W.-P., Munro M.H.G., Northcote P.T., and Prinsep M.R. Nat. Prod. Rep. 24 (2007) 31-86
8. Gavagnin M., and Fontana A. Curr. Org. Chem. 4 (2000) 1201-1248
9. Goldsmith D. In: ApSimon J. (Ed). The Total Synthesis of Tri- and Tetracyclic Diterpenes Vol. 8 (1992), John Wiley and Sons, New York, NY 228-230
10. Kazlauskas R., Murphy P.T., Wells R.J., Noack K., Oberhaensli W.E., and Schoenholzer P. Aust. J. Chem. 32 (1979) 867-880
11. Cimino G., De Rosa D., De Stefano S., and Minale L. Tetrahedron 30 (1974) 645-649
12. Keyzers R.A., Northcote P.T., and Davies-Coleman M.T. Nat. Prod. Rep. 23 (2006) 321-334
13. González M.A. Curr. Bioact. Comp. 3 (2007) 1-36
14. Imamura P.M., Sierra M.G., and Rúveda E.A. J. Chem. Soc., Chem. Commun. (1981) 734-735
15. Bory S., Fétizon M., and Laszlo P. Bull. Soc. Chim. Fr. (1963) 2310-2322
16. Nakano T., and Hernández M.I. Tetrahedron Lett. 23 (1982) 1423-1426
17. Nakano T., and Hernández M.I. J. Chem. Soc., Perkin Trans. 1 (1983) 135-139
18. Imamura P.M., and Rúveda E.A. J. Org. Chem. 45 (1980) 510-515
19. De Miranda D.S., Brendolan G., Imamura P.M., González Sierra M., Marsaioli A.J., and Rúveda E.A. J. Org. Chem. 46 (1981) 4851-4858
20. Vlad P.F., and Ungur N.D. Khim. Prir. Soedin. 6 (1984) 725-731
21. Vlad P.F., Ungur N.D., and Koltsa M.N. Tetrahedron 39 (1983) 3947-3958
22. Ungur N.D., and Vlad P.F. Khim. Prir. Soedin. 1 (1985) 45-51
23. Mischne M.P., González Sierra M., and Rúveda E.A. J. Org. Chem. 49 (1984) 2035-2037
24. González Sierra M., Mischne M.P., and Rúveda E.A. Synth. Commun. 15 (1985) 727-735
25. Nakano T., Hernández M.I., Gomez M., and Domingo Medina J. J. Chem. Res., Synop. (1989) 54-55
26. Urones J.G., Marcos I.S., Basabe P., Gomez A., Estrella A., and Lithgow A.M. Nat. Prod. Lett. 5 (1994) 217-220
27. Urones J.G., Sexmero M.J., Lithgow A.M., Basabe P., Gomez A., Marcos I.S., Estrella A., Diez D., Carballares S., and Broughton H.B. Nat. Prod. Lett. 6 (1995) 285-290
28. Basabe P., Gómez A., Marcos I.S., Martín D.D., Broughton H.B., and Urones J.G. Tetrahedron Lett. 40 (1999) 6857-6860
29. Abad A., Agulló C., Arnó M., Domingo L.R., and Zaragozá R.J. Org. Prep. Proced. Int. 23 (1991) 321-356
30. Lee H.-J., Ravn M.M., and Coates R.M. Tetrahedron 57 (2001) 6155-6167
31. Abad A., Arnó M., Domingo L.R., and Zaragozá R.J. Tetrahedron 41 (1985) 4937-4940
32. Ishihara K., Ishibashi H., and Yamamoto H. J. Am. Chem. Soc. 123 (2001) 1505-1506
33. Abad A., Agulló C., Arnó M., Marín M.L., and Zaragozá R.J. J. Chem. Soc., Perkin Trans. 1 (1996) 2193-2199
34. Abad A., Arnó M., Marín M.L., and Zaragozá R.J. Synlett (1991) 789-791
35. Abad A., Arnó M., Cuñat A.C., Marín M.L., and Zaragozá R.J. J. Org. Chem. 57 (1992) 6861-6869
36. Abad A., Arnó M., Marin M.L., and Zaragozá R.J. J. Chem. Soc., Perkin Trans. 1 (1993) 1861-1867
37. Arnó M., González M.A., Marín M.L., and Zaragozá R.J. Tetrahedron Lett. 42 (2001) 1669-1671
38. Arnó M., González M.A., and Zaragozá R.J. J. Org. Chem. 68 (2003) 1242-1251
39. Blake A.J., González M.A., and Gil-Gimeno M.J. Acta Crystallogr. C62 (2006) 208-210
40. Betancur-Galvis L., Zuluaga C., Arnó M., González M.A., and Zaragozá R.J. J. Nat. Prod. 65 (2002) 189-192
41. Arnó M., Betancur-Galvis L., González M.A., Sierra J., and Zaragozá R.J. Bioorg. Med. Chem. 11 (2003) 3171-3177
42. Arnó M., González M.A., and Zaragozá R.J. Tetrahedron 55 (1999) 12419-12428
43. Somerville M.J., Mollo E., Cimino G., Rungprom W., and Garson M.J. J. Nat. Prod. 69 (2006) 1086-1088
44. Abad A., Agulló C., Cuñat A.C., and García A.B. Tetrahedron Lett. 43 (2002) 7933-7936
45. Abad A., Agulló C., Cuñat A.C., García A.B., and Giménez-Saiz C. Tetrahedron 59 (2003) 9523-9536
46. Abad A., Agulló C., Cuñat A.C., and García A.B. Tetrahedron 61 (2005) 1961-1970
47. Kolympadi M., Liapis M., and Ragoussis V. Tetrahedron 61 (2005) 2003-2010
48. Eschenmoser A., Ruzicka L., Jeger O., and Arigoni D. Helv. Chim. Acta 38 (1955) 1890-1904
49. Stork G., and Burgstahler A.W. J. Am. Chem. Soc. 77 (1955) 5068-5077
50. Bartlett P.A. In: Morrison J.D. (Ed). Asymmetric Synthesis Vol. 3 (1984), Academic, New York, NY 341-409
51. Sutherland J.K. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 3 (1991), Pergamon, Oxford 341-377
52. Corey E.J., Lee J., and Roberts B.E. Tetrahedron Lett. 38 (1997) 8915-8918
53. Corey E.J., and Roberts B.E. Tetrahedron Lett. 38 (1997) 8919-8920
54. Corey E.J., and Wood Jr. H.B. J. Am. Chem. Soc. 118 (1996) 11982-11983
55. Huang A.X., Xiong Z., and Corey E.J. J. Am. Chem. Soc. 121 (1999) 9999-10003
56. Ishihara K., Nakamura S., and Yamamoto H. J. Am. Chem. Soc. 121 (1999) 4906-4907
57. Bogenstätter M., Limberg A., Overman L.E., and Tomasi A.L. J. Am. Chem. Soc. 121 (1999) 12206-12207
58. Ungur N., Kulcitki V., Gavagnin M., Castelluccio F., Vlad P.F., and Cimino G. Tetrahedron 58 (2002) 10159-10165
59. Nishizawa M., Takenaka H., and Hayashi Y. Chem. Lett. (1983) 1459-1460
60. Nishizawa M., Takenaka H., and Hayashi Y. J. Org. Chem. 51 (1986) 806-813
61. Vlad P.F., Ungur N.D., and Perutskii V.B. Khim. Prir. Soedin. 4 (1986) 514-515
62. Ungur N.D., Van Nguyen T., and Vlad P.F. Khim. Prir. Soedin. 5 (1991) 726-728
63. Nishizawa M., Yamada H., and Hayashi Y. J. Org. Chem. 52 (1987) 4878-4884
64. Pandey U.C., Sarmah P., and Sharma R.P. Tetrahedron 40 (1984) 3739-3748
65. Breslow R., Barrett E., and Mohacsi E. Tetrahedron Lett. 3 (1962) 1207-1211
66. Breslow R., Olin S.S., and Groves J.T. Tetrahedron Lett. 9 (1968) 1837-1840
67. Malacria M. Chem. Rev. 96 (1996) 289-306
68. Zoretic P.A., Weng X., Caspar M.L., and Davis D.G. Tetrahedron Lett. 32 (1991) 4819-4822
69. Snider B.B. Chem. Rev. 96 (1996) 339-363
70. Zoretic P.A., Shen Z., Wang M., and Ribeiro A.A. Tetrahedron Lett. 36 (1995) 2925-2928
71. Ribeiro A.A., Shen Z., Wang M., Zhang Y., and Zoretic P.A. Magn. Reson. Chem. 36 (1998) 325-335
72. Zoretic P.A., Zhang Y., and Ribeiro A.A. Tetrahedron Lett. 36 (1995) 2929-2932
73. Zoretic P.A., Wang M., Zhang Y., Shen Z., and Ribeiro A.A. J. Org. Chem. 61 (1996) 1806-1813
74. Zoretic P.A., Zhang Y., Fang H., Ribeiro A.A., and Dubay G. J. Org. Chem. 63 (1998) 1162-1167
75. Boehm H.M., Handa S., Pattenden G., Roberts L., Blake A.J., and Li W.-S. J. Chem. Soc., Perkin Trans. 1 (2000) 3522-3538
76. Handa S., Nair P.S., and Pattenden G. Helv. Chim. Acta 83 (2000) 2629-2643
77. Pattenden G., and Roberts L. Tetrahedron Lett. 37 (1996) 4191-4194
78. Pattenden G., Roberts L., and Blake A.J. J. Chem. Soc., Perkin Trans. 1 (1998) 863-868
79. Goeller F., Heinemann C., and Demuth M. Synthesis 8 (2001) 1114-1116
80. Baba Y., Sakamoto T., and Kanematsu K. Tetrahedron Lett. 35 (1994) 5677-5680
81. Sakamoto T., and Kanematsu K. Tetrahedron 51 (1995) 5771-5780
82. Mehta G., and Thomas A. Synth. Commun. 22 (1992) 1831-1838
83. Mayelvaganan T., Hadimani S., and Bhat S.V. Tetrahedron 53 (1997) 2185-2188
84. Weisser R., Yue W., and Reiser O. Org. Lett. 7 (2005) 5353-5356
85. Lebsack A.D., Overman L.E., and Valentekovich R.J. J. Am. Chem. Soc. 123 (2001) 4851-4852
86. Brady T.P., Kim S.H., Wen K., and Theodorakis E.A. Angew. Chem., Int. Ed. 43 (2004) 739-742
87. Brady T.P., Kim S.H., Wen K., Kim C., and Theodorakis E.A. Chem.-Eur. J. 11 (2005) 7175-7190
88. Guizzunti G., Brady T.P., Malhotra V., and Theodorakis E.A. J. Am. Chem. Soc. 128 (2006) 4190-4191