Chapter 2 Total synthesis of (±)-cylindrospermopsin

Strategies and Tactics in Organic Synthesis

Volumn 4, Issue C, 2004, Pages 19-39

  Snider, Barry B ^a   Xie, Chaoyu ^a  

^a BRANDEIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33645416659     PISSN: 18746004     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S1874-6004(04)80006-6     Document Type: Chapter

References (63)

1. For the primary reports of the synthesis described in this chapter see. Snider B.B., and Harvey T.C. Tetrahedron Lett. 36 (1995) 4587
2. Snider B.B., and Xie C. Tetrahedron Lett. 59 (1998) 7021
3. Xie C., Runnegar M.T.C., and Snider B.B. J. Am. Chem. Soc 722 (2000) 5017
4. Xie C. Ph. D. Thesis (2000), Brandeis University
5. Ohtani I., Moore R.E., and Runnegar M.T.C. J. Am. Chem. Soc 114 (1992) 7941
6. Moore R.E., Ohtani I., Moore B.S., De Koning C.B., Yoshida W.Y., Runnegar M.T.C., and Carmichael W.W. Gazz. Chim. Ital 123 (1993) 329
7. Burgoyne D.L., Hemscheidt T.K., Moore R.E., and Runnegar M.T.C. J. Org. Chem. 65 (2000) 152
8. Banker R., Teltsch B., Sukenik A., and Carmeli S. J. Nat. Prod. 63 (2000) 387
9. Norris R.L., Eaglesham G.K., Pierens G., Shaw G.R., Smith M.J., Chiswell R.K., Seawright A.A., and Moore M.R. Environ. Toxicol. 14 (1999) 163
10. Heintzelman G.R., Fang W.K., Keen S.P., Wallace G.A., and Weinreb S.M. J. Am. Chem. Soc. 123 (2001) 8851
11. Heintzelman G.R., Fang W.K., Keen S.P., Wallace G.A., and Weinreb S.A. J. Am. Chem. Soc. 124 (2002) 3939
12. For another synthesis of 7-epicylindrospermopsin see. White J.D., and Hansen J.D. For other synthetic work see. J. Am. Chem. Soc. 124 (2002) 4950
13. Heintzelman G.R., Parvez M., and Weinreb S.M. Synlett (1993) 551
14. Heintzelman G.R., Weinreb S.M., and Parvez M. J. Org. Chem. 61 (1996) 4594
15. McAlpine I.J., and Armstrong R.W. Tetrahedron Lett. 41 (2000) 1849
16. Keen S.P., and Weinreb S.M. Tetrahedron Lett. 41 (2000) 4307
17. Djung J.F., Hart D.J., and Young E.R.R. J. Org. Chem. 65 (2000) 5668
18. Looper R.E., and Williams R.M. Tetrahedron Lett. 42 (2001) 769
19. For recent reviews see. Murphy P.J., and Thomas C.W. Chem. Soc. Rev. 30 (2001) 303
20. Griffiths D.J., and Saker M.L. Environ. Toxicol 18 (2003) 78
21. Yamaguchi R., Nakazono Y., and Kawanisi M. Tetrahedron Lett. 24 (1983) 1801
22. Yamaguchi R., Nakazono Y., Matsuki T., Hata E.-L., and Kawanisi M. Bull Chem. Soc. Jpn. 60 (1987) 215
23. Gershon H. J. Org. Chem. 27 (1962) 3507
24. Stogryn E.L. J. Heterocycl Chem. 11 (1974) 251
25. Matsumoto M., Ishide Y., and Watanabe N. Heterocycles 23 (1985) 165
26. Bettoni G., Cellucci C., Ferorelli S., Perrone R., and Tortorella V. Tetrahedron 42 (1986) 2117
27. Tramontini M. Synthesis (1982) 605
28. Takahashi T., Kotsubo H., and Koizumi T. J. Chem. Soc., Perkin Trans. 1 (1991) 1677
29. Wada A., Yamamoto J., Hase T., Nagai S., and Kanatomo S. Synthesis (1986) 555
30. Uno H., Terakawa T., and Suzuki H. Synthesis (1989) 381
31. Khan M.W., and Kundu N.G. J. Chem. Res., Synop. (1999) 20
32. Griengl H., Wanek E., Schwarz W., Streicher W., Rosenwirth B., and De Clercq E. J. Med. Chem. 30 (1987) 1199
33. Kundu N.G., Choudhuri L.N., and Das B. J. Chem. Soc, Perkin Trans. 1 (1989) 1165
34. Maruyama T., Kimura S., and Honjo M. Org. Prep. Proced. Int. 20 (1988) 485
35. Murray K., Rasmussen P.S., Neustaedter J., and Luck J.M. J. Biol. Chem. 240 (1965) 705
36. Profft E., and Schulz G. Arch. Pharm. 294 (1961) 292
37. Profft, E., Krueger W., Kuhn P., Lietz W., Ger. Pat. (East), 69,126.
38. Chem. Abstr. 72 (1970) 90309w
39. Taylor Jr. E.C., and Crovetti A.J. In: Rabjohn N. (Ed). Organic Syntheses Collective Volume IV (1963), Wiley, New York 654-656
40. Comins D.L., and Brown J.D. Tetrahedron Lett. 27 (1986) 4549
41. Comins D.L., Weglarz M.A., and O'Connor S. Tetrahedron Lett. 29 (1988) 1751
42. Brown J.D., Foley M.A., and Comins D.L. J. Am. Chem. Soc. 110 (1988) 7445
43. Comins D.L., Joseph S.P., and Goehring R.R. J. Am. Chem. Soc. 116 (1994) 4719
44. Comins D.L., and Dehghani A. J. Org. Chem. 60 (1995) 794
45. Comins D.L., Joseph S.P., Hong H., Al-awan R.S., Foti C.J., Zhang Y.-M., Chen X., LaMunyon D.H., and Weltzien M.G. Pure Appl. Chem. 69 (1997) 411
46. Comins D.L., LaMunyon D.H., and Chen X. J. Org. Chem. 62 (1997) 8182
47. Corey E.J., and Boaz N.W. Tetrahedron Lett. 26 (1985) 6015
48. Alexakis A., Berlan J., and Besace Y. Tetrahedron Lett. 27 (1986) 1047
49. Bertz S.H., Miao G., Rossiter B.E., and Snyder J.P. J. Am. Chem. Soc. 117 (1995) 11023
50. Yong Y.F., Kowalski J.A., and Lipton M.A. J. Org. Chem. 62 (1997) 1540
51. Lee S.Y., Niwa M., and Snider B.B. J. Org. Chem. 53 (1988) 2356
52. Veysoglu T., Mitscher L.A., and Swayze J.K. Synthesis (1980) 807
53. Borch R.F., Bernstein M.D., and Durst H.D. J. Am. Chem. Soc. 93 (1971) 2897
54. Bordner J., Thiessen W.E., Bates H.A., and Rapoport H. J. Am. Chem. Soc. 97 (1975) 6008
55. Schmidtchen F.P., Oswald H., and Schummer A. Liebigs Ann. Chem. (1991) 539
56. Dyson G.M., George H.J., and Hunter R.F. J. Chem. Soc. (1927) 436
57. Siddiqui S., Begum S., and Siddiqui B.S. Z Naturforsch. 37b (1982) 1481
58. Siddiqui S., Haider S.I., Ahmad S.S., and Siddiqui B.S. Z Naturforsch. 40b (1985) 546
59. Ahmad S.S., Haider S.I., and Fatima I. Synth. Commun. 17 (1987) 1861
60. In: Mulder G.R. (Ed). Sulfation of Drugs and Related Compounds (1981), CRC Press, Boca Raton, FL 51
61. Lubineau A., and Lemoine R. Tetrahedron Lett. 55 (1994) 8795
62. Futaki S., Taike T., Yagami T., Ogawa T., Akita T., and Kitagawa K. J. Chem. Soc., Perkin Trans. 1 (1990) 1739
63. Runnegar M.T., Kong S.-M., Zhong Y.-Z., Ge J.L., and Lu S.C. Biochem. Biophys. Res. Commun. 201 (1994) 235