Chapter Three Synthesis and Structure- Activity Studies of Lissoclinum Peptide Alkaloids

Alkaloids: Chemical and Biological Perspectives

Volumn 12, Issue C, 1998, Pages 187-228

  Wipf, Peter ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77957075752     PISSN: 07358210     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S0735-8210(98)80005-8     Document Type: Chapter

References (113)

1. Faulkner D.J. Nat Prod Rep 13 (1996) 75
2. Faulkner D.J. Nat Prod Rep 12 (1995) 233
3. Flam F. Science 266 (1994) 1324
4. Faulkner D.J. Nat Prod Rep 11 (1994) 355
5. In: Attaway D.H., and Zaborsky O.R. (Eds). Marine Biotechnology, Volume 1: Pharmaceutical and Bioactive Marine Natural Products (1993), Plenum Publishers, New York
6. Faulkner D.J. Chem Rev 93 (1993) 1671
7. See, for example:. Wipf P., and Lim S. Chimia 50 (1996) 157
8. Hung D.T., Nerenberg J.B., and Schreiber S.L. Chem Biol 1 67 (1994)
9. Fukuyama T., and Xu L. J Am Chem Soc 115 (1993) 8449
10. Degnan B.M., Hawkins C.J., Lavin M.F., McCaffrey E.J., Parry D.L., and Watters D.J. J Med Chem 32 (1989) 1354
11. Foster M.P., Concepcion G.P., Caraan G.B., and Ireland C.M. J Org Chem 57 (1992) 6671
12. Hambley T.W., Hawkins C.J., Lavin M.F., Brenk A., and Watters D.J. Tetrahedron 48 (1992) 341
13. Prinsep M.R., Moore R.E., Levine I.A., and Patterson G.M.L. J Nat Prod 55 (1992) 140
14. Ogino J., Moore R.E., Patterson G.M.L., and Smith C.D. J Nat Prod 59 (1996) 581
15. Ojika M., Nemoto T., Nakamura M., and Yamada K. Tetrahedron Lett 36 (1995) 5057
16. Nakamura M., Shibata T., Nakane K., Nemoto T., Ojika M., and Yamada K. Tetrahedron Lett 36 (1995) 5059
17. Todorova A.K., Jüttner F., Linden A., Plüss T., and von Philipsborn W. J Org Chem 60 (1995) 7891
18. Admi V., Afek U., and Carmeli S. J Nat Prod 59 (1996) 396
19. Wasylyk J.M., Biskupiak J.E., Costello C.E., and Ireland C.M. J Org Chem 48 (1983) 4445
20. Degnan B.M., Hawkins C.J., Lavin M.F., McCaffrey E.J., Parry D.L., Van den Brenk A.L., and Watters D.J. J Med Chem 32 (1989) 1349
21. Schmitz F.J., Ksebati M.B., Chang J.S., Wang J.L., Hossain M.B., Van der Helm D., Engel M.H., Serban A., and Silfer J.A. J Org Chem 54 (1989) 3463
22. Boden C.D.J., and Pattenden G. Tetrahedron Lett 36 (1995) 6153
23. Boden C., and Pattenden G. Tetrahedron Lett 35 (1994) 8271
24. Hawkins C.J., Lavin M.F., Marshall K.A., Van den Brenk A.L., and Watters D.J. J Med Chem 33 (1990) 1634
25. Wipf P., and Fritch P.C. J Am Chem Soc 118 (1996) 12358
26. Ireland C.M., Durso A.R., Newman R.A., and Hacker M.P. J Org Chem 47 (1982) 1807
27. Toske S.G., and Fenical W. Tetrahedron Lett 36 (1995) 8355
28. Boden C.D.J., Norley M.C., and Pattenden G. Tetrahedron Lett 37 (1996) 9111
29. Hamamoto Y., Endo M., Nakagawa M., Nakanishi T., and Mizukawa K. J Chem Soc Chem Commun 323 (1983)
30. Hamada Y., Kato S., and Shioiri T. Tetrahedron Lett 26 (1985) 3223
31. Ireland C.M., Durso A.R., Newman R.A., and Hacker M.P. J Org Chem 47 (1982) 1807
32. Hamada Y., Shibata M., and Shioiri T. Tetrahedron Lett 26 (1985) 6501
33. Hamada Y., Shibata M., and Shioiri T. Tetrahedron Lett 26 (1985) 5159
34. Schmidt U., and Griesser H. Tetrahdron Lett 27 (1986) 163
35. McDonald L.A., and Ireland C.M. J Nat Prod 55 (1992) 376
36. Rashid M.A., Gustafson K.R., Cardellina J.H., and Boyd M.R. J Nat Prod 58 (1995) 594
37. Ireland C., and Scheuer P.J. J Am Chem Soc 102 (1980) 5688
38. Biskupiak J.E., and Ireland C.M. J Org Chem 48 (1983) 2302
39. McDonald L.A., Foster M.P., Phillips D.R., Ireland C.M., Lee A.Y., and Clardy J. J Org Chem 57 (1992) 4616
40. and references cited therein. Davidson B.S. Chem Rev 93 (1993) 1771
41. and references cited therein. Taylor S.W., Kammerer B., and Bayer E. Chem Rev 97 (1997) 333
42. Shin J., and Fenical W. J Org Chem 56 (1991) 3392
43. Cox G. New Phytol. 104 (1986) 429
44. Wipf P., and Fritch P.C. Tetrahedron Lett 35 (1994) 5397
45. Pettit G.R., Kamano Y., Holzapfel C.W., Vanzyl W.J., Tuinman A.A., Herald C.L., Baczynskyj L., and Schmidt J.M. J Am Chem Soc 109 (1987) 7581
46. Wesson K.J., and Hamann M.T. J Nat Prod 59 (1996) 629
47. Carroll A.R., Bowden B.F., Coll J.C., Hockless D.C.R., Skelton B.W., and White A.H. Aust J Chem 47 (1994) 61
48. Carroll A.R., Coll J.C., Bourne D.J., MacLeod J.K., Zabriskie T.M., Ireland C.M., and Bowden B.F. Aust J Chem 49 (1996) 659
49. Mau C.M.S., Nakao Y., Yoshida W.Y., and Scheuer P.J. J Org Chem 61 (1996) 6302
50. Sesin D.F., Gaskell S.J., and Ireland C.M. Bull Soc Chim Belg 95 (1986) 853
51. Ireland C.M., Molinski T.F., Roll D.M., Zabriskie T.M., McKee T.C., Swersey J.C., and Foster M.P. In: Scheuer P.J. (Ed). Bioorganic Marine Chemistry Vol. 3 (1989), Springer, Berlin 1-46
52. Albizati K.F., Martin V.A., Agharahimi M.R., and Stolze D.A. In: J Scheuer P. (Ed). Bioorganic Marine Chemistry Vol. 6 (1991), Springer, Berlin 1-68
53. Part C. Shioiri T., and Hamada Y. In: Rahman A.-u. (Ed). Studies in Natural Products Chemistry. Stereoselective Synthesis Vol. 4 (1989), Elsevier, Amsterdam 83-110
54. Schmidt U. Pure Appl Chem 58 (1986) 295
55. Wipf P. Chem Rev 59 (1995) 2115
56. Meyers A.I., Hanagan M.A., and Mazzu A.L. Heterocycles 15 (1981) 361
57. Galeotti N., Montagne C., Poncet J., and Jouin P. Tetrahedron Lett 33 (1992) 2807
58. Wipf P., and Miller C.P. Tetrahedron Lett 33 (1992) 6267
59. Wipf P., and Miller C.P. Tetrahedron Lett 33 (1992) 907
60. Wipf P., and Venkatraman S. Tetrahedron Lett 37 (1996) 4659
61. For a general review on the synthesis of oxazolines see:. Gant T.G., and Meyers A.I. Tetrahedron 50 (1994) 2297
62. Wipf P., and Venkatraman S. Synlett 1 (1997)
63. Wipf P., and Miller C.P. J Org Chem 58 (1993) 3604
64. Evans D.L., Minster D.K., Jordis U., Hecht S.M., Mazzu A.L., and Meyers A.I. J Org Chem 44 (1979) 497
65. Barrish J.C., Singh J., Spergel S.H., Han W.-C., Kissick T.P., Kronenthal D.R., and Mueller R.H. J Org Chem 58 (1993) 4494
66. Meyers A.I., and Tavares F.X. J Org Chem 61 (1996) 8207
67. Evans D.A., Gage J.R., and Leighton J.L. J Am Chem Soc 114 (1992) 9434
68. Schmidt U., and Griesser H. Tetrahdron Lett 27 (1986) 163
69. Wipf P., and Miller C.P. J Am Chem Soc 114 (1992) 10975
70. Wipf P., and Venkatraman S. J Org Chem 60 (1995) 7224
71. Aguilar E., and Meyers A.I. Tetrahedron Lett 35 (1994) 2477
72. North M., and Pattenden G. Tetrahedron 46 (1990) 8267
73. Boden C.D.J., Pattenden G., and Ye T. Synlett 417 (1995)
74. Clausen K., Thorsen M., Lawesson S.O., and Spatola A.F. J Chem Soc Perkin Trans 1 785 (1984)
75. Hoeg-Jensen T., Holm A., and Sorensen H. Synthesis 383 (1996)
76. Wipf P., Miller C.P., Venkatraman S., and Fritch P.C. Tetrahedron Lett 36 (1995) 6395
77. Schmidt U., and Gleich P. Monatsh Chem 116 (1985) 1459
78. Bredenkamp M.W., Holzapfel C.W., Synman R.M., and Van Zyl W.J. Syn Commun 22 (1992) 3029
79. Aguilar E., and Meyers A.I. Tetrahedron Lett 35 (1994) 2473
80. Sowinski J.A., and Toogood P.L. J Org Chem 61 (1996) 7671
81. Hamada Y., Shibata M., Sugiura T., Kato S., and Shioiri T. J Org Chem 52 (1987) 1252
82. Wipf P., and Xu W. J Org Chem 61 (1996) 6556
83. Shioiri T., Ninomiya K., and Yamada S. J Am Chem Soc 94 (1972) 6203
84. Shioiri T., Yokoyama Y., Kasai Y., and Yamada S. Tetrahedron 32 (1976) 2211
85. Lajoie G., Lepine F., Maziak L., and Belleau B. Tetrahedron Lett 24 (1983) 3815
86. Zacharie B., Sauve G., and Penney C. Tetrahedron 49 (1993) 10489
87. Chen S., and Xu J. Tetrahedron Lett 32 (1991) 6711
88. Dudash J., Jiang J., Mayer S.C., and Joullié M. Synth Commun 23 (1993) 349
89. Wipf P., and Miller C.P. J Org Chem 58 (1993) 1575
90. Moody C.J., and Bagley M.C. Synlett 1171 (1996)
91. Bagley M.C., Buck R.T., Hind S.L., Moody C.J., and Slawin A. Synlett 825 (1996)
92. Ishida T., Inoue M., Hamada Y., Kato S., and Shioiri T. J Chem Soc Chem Commun 370 (1987)
93. Ishida T., Tanaka M., Nabae M., Inoue M., Kato S., Hamada Y., and Shioiri T. J Org Chem 53 (1988) 107
94. Ishida T., In Y., Doi M., Inoue M., Hamada Y., and Shioiri T. Biopolymers 32 (1992) 131
95. In Y., Doi M., Inoue M., Ishida T., Hamada Y., and Shioiri T. Chem Pharm Bull 41 (1993) 1686
96. In Y., Doi M., Inoue M., Ishida T., Hamada Y., and Shioiri T. Acta Cryst C50 (1994) 432
97. Ishida T., Ohishi H., Inoue M., Kamigauchi M., Sugiura M., Takao N., Kato S., Hamada Y., and Shioiri T. J Org Chem 54 (1989) 5337
98. Venkatachalam C.M. Biopolymers 6 (1968) 1425
99. Ishida T., In Y., Shinozaki F., Doi M., Yamamoto D., Hamada Y., Shioiri T., Kamigauchi M., and Sugiura M. J Org Chem 60 (1995) 3944
100. P Wipf, S Venkatraman, CP Miller, and CM Grant, unpublished results.
101. Abbenante G., Fairlie D.P., Gahan L.R., Hanson G.R., Pierens G.K., and van den Brenk A.L. J Am Chem Soc 118 (1996) 10384
102. v d Brenk A., Fairlie D.P., Gahan L.R., Hanson G.R., and Hambley T.W. Inorg Chem 35 (1996) 1095
103. Sessler J.L., and Burrell A.K. Top Curr Chem 161 (1991) 177
104. Bradshaw J.S., Krakowiak K.E., and Izatt R.M. Aza-crown Macrocycles (1993), Wiley, New York
105. Michael J.P., Pattenden G., and Chem A. Int Ed Engt 32 (1993) 1
106. Wipf P., Vcnkatraman S., Miller C.P., and Geib S.J. Angew Chem Int Ed Engl 33 (1994) 1516
107. Van den Brenk A.L., Byriel K.A., Fairlie D.P., Gahan L.R., Hanson G.R., Hawkins C.J., Jones A., Kennard C.H.L., Moubaraki B., and Murray K.S. Inorg Chem 33 (1994) 3549
108. Van den Brenk A.L., Fairlie D.P., Hanson G.R., Gahan L.R., Hawkins C.J., and Jones A. Inorg Chem 33 (1994) 2280
109. Kohda K., Ohta Y., Yokoyama Y., Kawazoe Y., Kato T., Suzumura Y., Hamada Y., and Shioiri T. Biochem Pharm 38 (1989) 4497
110. Kohda K., Ohta Y., Kawazoe Y., Kato T., Suzumura Y., Hamada Y., and Shioiri T. Biochem Pharm 38 (1989) 4500
111. Williams A.B., and Jacobs R.S. Cancer Lett 71 (1993) 97
112. Shioiri T., Hamada Y., Kato S., Shibata M., Kondo Y., Nakagawa H., and Kohda K. Biochem Pharm 36 (1987) 4181
113. For a structure-activity analysis of a tris-oxazoline analog vs the tris-thiazoline-containing natural product thiangazole, see [55].