Intramolecular cyclization strategies toward the synthesis of zoanthamine alkaloids

Tetrahedron Letters

Volumn 52, Issue 38, 2011, Pages 4920-4923

  Fischer, Derek ^a   Nguyen, Thong X ^a   Trzoss, Lynnie ^a   Dakanali, Marianna ^a   Theodorakis, Emmanuel A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Aminodiene; Cycloaddition; Diels Alder reaction; Stille coupling; Zoanthamine

Indexed keywords

ALKALOID DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG; ZOANTHAMINE ALKALOID DERIVATIVE;

ARTICLE; CYCLIZATION; CYCLOADDITION; DIELS ALDER REACTION; DRUG STRUCTURE; DRUG SYNTHESIS;

ALNUS;

EID: 84860404836     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.07.054     Document Type: Article

References (50)

1. C.B. Rao, A.S.R. Anjaneyula, N.S. Sarma, Y. Venkatateswarlu, R.M. Rosser, D.J. Faulkner, M.H.M. Chen, and J. Clardy J. Am. Chem. Soc. 106 1984 7983 7984
2. For selected reviews on this topic, see: A.U. Rahman, and M.I. Choudhary Alkaloids Vol. 52 1999 Academic press New York 233 260
3. M. Kuramoto, K. Yamaguchi, T. Tsuji, and D. Uemura Zoanthamines, Antiosteoporotic Alkaloids N. Fusetani, Drugs from the Sea 2000 Karger Basel 98 106
4. K. Yamada, M. Kuramoto, and D. Uemura Rec. Res. Dev. Pure Appl. Chem. 3 1999 245 254
5. J.J. Fernandez, M.L. Souto, A.H. Daranas, and M. Norte Curr. Top. Phytochem. 4 2000 105 119
6. For a comprehensive review of the chemistry and biology of zoanthamines see: D.C. Behenna, J.L. Stockdill, and B.M. Stoltz Angew. Chem., Int. Ed. 47 2008 2365 2386
7. M. Kuramoto, K. Hayashi, Y. Fujitani, K. Yamaguchi, T. Tsuji, K. Yamada, Y. Ijuin, and D. Uemura Tetrahedron Lett. 38 1997 5683 5686
8. S. Fukuzawa, Y. Hayashi, D. Uemura, A. Nagatsu, K. Yamada, and Y. Ijuin Heterocycl. Commun. 1 1995 207 214
9. R.M. Villar, J. Gil-Longo, A.H. Daranas, M.L. Souto, J.J. Fernandez, S. Peixinho, M.A. Barral, G. Santafe, J. Rodriguez, and C. Jimenez Bioorg. Med. Chem. 11 2003 2301 2306
10. C.B. Rao, A.S.R. Anjaneyulu, N.S. Sarma, Y. Venkateswarlu, R.M. Rosser, and D.J. Faulkner J. Org. Chem. 50 1985 3757 3760
11. C.B. Rao, D.V. Rao, V.S.N. Raju, B.W. Sullivan, and D.J. Faulkner Heterocycles 28 1989 103 106
12. K. Yamaguchi, M. Yada, T. Tsuji, M. Kuramoto, and D. Uemura Biol. Pharm. Bull. 22 1999 920 928
13. M. Kuramoto, K. Hayashi, K. Yamaguchi, M. Yada, T. Tsuji, and D. Uemura Bull. Chem. Soc. Jpn. 71 1998 771 779
14. M. Miyashita, M. Sasaki, I. Hattori, M. Sakai, and K. Tanino Science 305 2004 495 499
15. Y. Murata, D. Yamashita, K. Kitahara, Y. Minasako, A. Nakazaki, and S. Kobayashi Angew. Chem., Int. Ed. 48 2009 1400 1403
16. D. Yamashita, Y. Murata, N. Hikage, K.I. Takao, A. Nakazaki, and S. Kobayashi Angew. Chem., Int. Ed. 48 2009 1404 1406
17. Y. Takahashi, F. Yoshimutra, K. Tanino, and M. Miyashita Angew. Chem., Int. Ed. 48 2009 8905 8908
18. F. Rivas, S. Ghosh, and E.A. Theodorakis Tetrahedron Lett. 46 2005 5281 5284
19. S. Ghosh, F. Rivas, D. Fischer, M.A. Gonzalez, and E.A. Theodorakis Org. Lett. 6 2004 941 944
20. T.X. Nguyen, M. Dakanali, L. Trzoss, and E.A. Theodorakis Org. Lett. 13 2011 3308 3311
21. D. Enders, and O. Meyer Liebigs Ann. 1996 1023 1035
22. J. Barluenga, A. Suarez-Sobrino, and L.A. Lopez Aldrichim. Acta 32 1999 4 15
23. W. Notz, F. Tanaka, and C.F. Barbas III Acc. Chem. Res. 37 2004 580 591
24. For selected reports on intermolecular Diels-Alder reaction of 2-aminodienes see: G. Pitacco, A. Risaliti, M.L. Trevisan, and E. Valentin Tetrahedron 33 1977 3145 3148
25. G. Marc, P. Nitti, G. Pitacco, A. Pizzioli, and E. Valentin J. Chem. Soc., Perkin Trans. 1 1997 223 228
26. J. Barluenga, F. Aznar, C. Valdes, A. Martin, S. Garcia-Granda, and E. Martin J. Am. Chem. Soc. 115 1993 4403 4404
27. C.S. Kniep, R. Boese, and R. Sustmann Tetrahedron 56 2000 4157 4162
28. J. Barluenga, C. Mateos, F. Aznar, and C. Valdes Org. Lett. 4 2002 1971 1974
29. For selected reports on intermolecular Diels-Alder of 2-amidodienes see: A. Trabocchi, and A. Guarna Org. Lett. 2 2000 1241 1242
30. F.L. Galbo, E.G. Occhiato, A. Guarna, and C. Faggi J. Org. Chem. 68 2003 6360 6368
31. J. Huang, H. Xiong, R.P. Hsung, C. Rameshkumar, J.A. Mulder, and T.P. Grebe Org. Lett. 4 2002 2417 2420
32. C.-C. Huang, and N.-C. Chang Org. Lett. 10 2008 673 676
33. S. Kobayashi, T. Furuya, T. Otani, and T. Saito Tetrahedron 64 2008 9705 9716
34. S. Kobayashi, T. Semba, T. Takahasi, S. Yoshida, K. Dai, T. Otani, and T. Saito Tetrahedron 65 2009 920 933
35. M. Movassaghi, D.K. Hunt, and M. Tjandra J. Am. Chem. Soc. 128 2006 8126 8127
36. M.V. Chelliah, S. Chackalamannil, Y. Xia, K. Eagen, M.C. Clasby, X. Gao, W. Greenlee, H.-S. Ahn, J. Agans-Fantuzzi, G. Boykow, Y. Hsieh, M. Bryant, J. Palamanda, T.-M. Chan, D. Hesk, and M. Chintala J. Med. Chem. 50 2007 5147 5160
37. M. Movassaghi, M. Tjandra, and J. Qi J. Am. Chem. Soc. 131 2009 9648 9650
38. N. Kataoka, Q. Shelby, J.P. Stambuli, and J.F. Hartwig J. Org. Chem. 67 2002 5553 5556
39. C.M. Marson, A. Khan, and R.A. Porter J. Org. Chem. 66 2001 4771 4775
40. E.L. Pearson, L.C.H. Kwan, C.I. Turner, G.A. Jones, A.C. Willis, M.N. Paddon-Row, and M.S. Sherburn J. Org. Chem. 71 2006 6099 6109
41. E.L. Pearson, A.C. Willis, M.S. Sherburn, and M.N. Paddon-Row Org. Biomol. Chem. 6 2008 513 522
42. E.L. Pearson, N. Kanizaj, A.C. Willis, M.N. Paddon-Row, and M.S. Sherburn Chem. Eur. J. 16 2010 8280 8284
43. F. Yoshimura, M. Sasaki, I. Hattori, K. Komatsu, M. Sakai, K. Tanino, and M. Miyashita Chem. Eur. J. 15 2009 6626 6644
44. M. Miyashita Pure Appl. Chem. 79 2007 651 665
45. M. Juhl, and D. Tanner Chem. Soc. Rev. 38 2009 2983 2992
46. D.M. Pinkerton, M.G. Banwell, and A.C. Willis Org. Lett. 11 2009 4290 4293
47. J.-P. Lumb, and D. Trauner J. Am. Chem. Soc. 127 2005 2870 2871
48. T. Imamoto, N. Takiyama, K. Nakamura, T. Hatajima, and Y. Kamiya J. Am. Chem. Soc. 111 1989 4392 4398
49. J.P. Burke, M. Sabat, W.H. Myers, and J.J. Chruma Tetrahedron: Asymmetry 22 2011 31 35
50. P.A. Clarke, R.L. Davie, and S. Peace Tetrahedron 61 2005 2335 2351