Aromatic alkaloids from ascidians

Studies in Natural Products Chemistry

Volumn 23, Issue C, 2000, Pages 233-283

  Bowden, Bruce F ^a  

^a JAMES COOK UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77957047508     PISSN: 15725995     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S1572-5995(00)80131-3     Document Type: Article

References (172)

1. Davidson B.S. Chem. Rev. 93 (1993) 1771
2. Davidson B.S. Chem. Rev. 94 (1994) 1719
3. Faulkner D.J. Nat. Prod. Rep. 1 (1984) 551
4. Faulkner D.J. Nat. Prod. Rep. 3 (1986) 1
5. Faulkner D.J. Nat. Prod. Rep. 4 (1987) 539
6. Faulkner D.J. Nat. Prod. Rep. 5 (1988) 613
7. Faulkner D.J. Nat. Prod. Rep. 7 (1990) 269
8. Faulkner D.J. Nat. Prod. Rep. 8 (1991) 97
9. Faulkner D.J. Nat. Prod. Rep. 9 (1992) 323
10. Faulkner D.J. Nat. Prod. Rep. 10 (1993) 497
11. Faulkner D.J. Nat. Prod. Rep. 11 (1994) 355
12. Faulkner D.J. Nat. Prod. Rep. 12 (1995) 223
13. Faulkner D.J. Nat. Prod. Rep. 13 (1996) 75
14. Searle P.A., and Molinski T.F. J. Org. Chem. 59 (1994) 6600
15. Ireland C.M., Durso A., and Scheuer P.J. J. Nat Prod. 44 (1981) 360
16. Sesin D.F., and Ireland C.M. Tetrahedron Lett. 25 (1984) 403
17. Arabshahi L., and Schmitz F. J. Tetrahedron Lett. 29 (1988) 1099
18. Copp B.R., Blunt J.W., Munro M.H.G., and Pannell L.K. Tetrahedron Lett. 30 (1989) 3703
19. Litaudon M., and Guyot M. Tetrahedron Lett. 32 (1991) 911
20. Behar V., and Danishefsky S.J. J. Amer. Chem. Soc. 115 (1993) 7017
21. Litaudon M., Trigalo F., Martin M.-T., Frapier F., and Guyot M. Tetrahedron 50 (1994) 5323
22. Makarieva T.N., Stonik V.A., Dmitrenok A.S., Grebnev B.B., Isakov V.V., Rebachyk N.M., and Rashkes Y.W. J. Nat. Prod 58 (1995) 254
23. Davidson B.S., Ford P.W., and Wahlman M. Tetrahedron lett. 35 (1994) 7185
24. Davidson B.S., Molinsky T.F., Barrows L.R., and Ireland C.M. J. Amer. Chem. Soc. 113 (1991) 4709
25. Ford P.W., and Davidson B.S. J. Org. Chem. 58 (1993) 4522
26. Ford P.W., Narbut M.R., Belli J., and Davidson B.S. J. Org. Chem. 59 (1994) 5955
27. Toste F.D., and Still W.J. J. Amer. Chem. Soc. 117 (1995) 7261
28. Compagnone R.S., and Faulkner D.J. Tetrahedron 50 (1994) 12785
29. Abas S.A., Hossain M.B., vanderHelm D., Schmitz F.J., Laney. M., Cabuslay R., and Schatzman R.C. J. Org. Chem. 61 (1996) 2709
30. Hirseh S., Miroz A., McCarthy P., and Kashman Y. Tetrahedron Lett. 30 (1989) 4291
31. Lindquist N., and Fenical W. Tetrahedron Lett. 31 (1990) 2521
32. McDonald L.A., Swersey J.C., Ireland C.M., Carroll A.R., Coll J.C., Bowden B.F., Fairchild C.R., and Cornell L. Tetrahedron 51 (1995) 5237
33. Miao S., and Andersen R.J. J. Org. Chem. 56 (1991) 6275
34. Taylor S.W., Kammerer B., and Bayer E. Chem. Rev. 97 (1997) 333
35. 1214Bruening R.C., Oltz E.M., Furukawa J., Nakanishi K., and Kustin K. J. Am. Chem. Soc. 107 (1985) 5298
36. Horenstein B.A., and Nakanishi K. J. Am. Chem. Soc. 111 (1989) 6242
37. Bayer E., Schiefer G., Waidelich D., Scippa S., and De Vincentiis M. Angew. Chem. lnt. Ed. Eng. 31 (1992) 52
38. Oltz E.M., Bruening R.C., Smith M.J., Kustin K., and Nakanishi K. J. Am. Chem. Soc. 110 (1988) 6162
39. Azumi K., Yokosawa H., and Ishii S.-i. Biochemistry 29 (1990) 149
40. Carroll A.R., Feng Y., Bowden B.F., and Coil J.C. J. Org. Chem. 61 (1996) 4059
41. Feng Y., and Bowden B.F. Aust.J. Chem. 50 (1997) 337
42. Kobayashi, J.; Cheng, J-f.; Kikuchi, Y.; Ishibashi, M.; Yamamura, S.; Ohizumi, Y.; Ohta, T.; Nozoe, S. Tetrahedron Lett., 31, 4617.
43. Yoshida W.Y., Lee K.K., Carroll A.R., and Scheuer P.J. Helv. Chim. Acta 75 (1992) 1721
44. Rudi A., Goldberg I., Stein Z., Frolow F., Benayahu Y., Schleyer M., and Kashman Y. J. Org. Chem. 59 (1994) 999
45. Terpin A., Polbom K., and Steglich W. Tetrahedron 51 (1995) 9941
46. Urban S., Butler M.S., and Capon R.J. Aust. J. Chem. 47 (1994) 1919
47. Urban S., Hobbs L., Hooper J.N.A., and Capon R.J. Aust. J. Chem. 48 (1995) 1491
48. Banwell M.J., Flynn B.L., Hamel E., and Hockless D.C.R. J. Chem. Soc. Chem. Commun. (1997) 207
49. Kang H., and Fenical W. J. Org. Chem. 62 (1997) 3254
50. Andersen R.J., Faulkner D.J., Cun-heng H., Van Duyne G.G., and Clardy J. J. Amer. Chem. Soc. 107 (1985) 5492
51. Lindquist N., Fenical W., VanDuyne G.G., and Clardy J. J. Org. Chem. 53 (1988) 4570
52. Kock M., Reif B., Fenical W., and Griesinger C. Tetrahedron Lett. 37 (1996) 363
53. Reif B., Kock M., Kerssebaum R., Kang H., Fenical W., and Griesinger C. J. Mag. Res. Ser. A 118 (1996) 282
54. Heim A., Terpin A., and Steglich W. Angew. Chem. Int. Ed. Eng. 36 (1997) 155
55. Carroll A.R., Bowden B.F., and Coil J.C. Aust. J. Chem. 46 (1993) 489
56. Urban S., and Capon R.J. Aust. J. Chem. 49 (1996) 711
57. Reddy M.V.R., Faulkner D.J., Venkateswarlu M., and Rao M.R. Tetrahedron 53 (1997) 3457
58. Quesada A.R., Gravalos M.D.G., and Puentes J.L.F. Br. J. Cancer 74 (1996) 677
59. Chan G.W., Francis T., Thureen D.R., Often P.H., Pierce N.J., Westley J.W., Johnson R.K., and Faulkner D.J. J. Org. Chem. 58 (1993) 2544
60. Palermo J.A., Brasco M.F.R., and Seldes A.M. Tetrahedron 52 (1996) 2727
61. Rinehart K.L., Holt T.G., Fregeau N.L., Stroh J.G., Keifer P.A., Sun F., Li L.H., and Martin D.G. J. Org. Chem. 55 (1990) 4512
62. Wright A.E., Forleo D.A., Gunawardana G.P., Gunasekera S.P., Koehn F.E., and McConnell O. J. Org. Chem. 55 (1990) 4508
63. Kubo A., and Saito N. Studies in Natural Products Chemistry (1992), Elsevier Science B.V, Amsterdam 77-145
64. He H., and Faulkner D.J. J. Org. Chem. 54 (1989) 5822
65. Davidson B.S. Tetrahedron Lett. 33 (1992) 3721
66. Sakai R., Rinehart K.L., Guan Y., and Wang A.H.J. Proc. Nat. Acad. Sci. USA 89 (1992) 11456
67. Guan Y., Rinehart K.L., and Wang A.H.J. J. Biomol. Struct. Dyn. 10 (1993) 793
68. Sakai R., Jareserijman E.A., Manzanares I., Elipe M.V.S., and Rinehart K.L. J. Am. Chem. Soc. 118 (1996) 9017
69. Kerr R.G., and Miranda N.F. J. Nat. Prod 58 (1995) 1618
70. Saito N., Tashiro K., Maru Y., Yamaguchi K., and Kubo A. J. Chem. Soc. Perkin Trans. 1 (1997) 53
71. Rinehart K., and Sakai R. PCT Int. Appl. (1992)
72. Pommier Y., Kohlhagen G., Bailly C., Waring M., Mazumder A., and Kohn K.W. (C.A. 117, 205189z). Biochemistry 35 (1996) 13303
73. Reid J.M., Walker D.L., and Ames M.M. Cancer Chemother. Pharmacol. 38 (1996) 329
74. Corey E.J., Gin D.Y., and Kania R.S. J. Am. Chem. Soc. 118 (1996) 9202
75. Corey E.J., and Gin D.Y. Tetrahedron Lett. 37 (1996) 7163
76. Niwa H., Yoshida Y., and Yamada K. J. Nat. Prod 51 (1988) 343
77. Fahey E., Potts B.C.M., Faulkner D.J., and Smith K. J.Nat. Prod. 54 (1991) 564
78. Debitus C., Laurent D., and Pais M. J. Nat. Prod 51 (1988) 799
79. Somei M., Kobayashi K., Tanii K., Mochizuki T., Kawada Y., and Fukui Y. Heterocycles 40 (1995) 119
80. Moquin C., and Guyot M. Tetrahedron Lett. 25 (1984) 5047
81. Heitz S., Durgeoat M., Guyot M., Brassy C., and Bachet B. Tetrahedron Lett. 21 (1980) 1457
82. Guyot M., and Meyer M. Tetrahedron Lett. 27 (1986) 2621
83. Bergmann T., Schories D., and Steffan B. Tetrahedron 53 (1987) 2055
84. Hogan I.T., and Sainsbury M. Tetrahedron 40 (1984) 681
85. Moquin-Pattey C., and Guyot M. Tetrahedron 45 (1989) 3445
86. Vervoort H.C., Richards-Gross S.E., Fenical W., Lee A.Y., and Clardy J. J. Org. Chem. 62 (1997) 1486
87. Tsukamoto S., Hirota H., Kato H., and Fusetani N. Tetrahedron Lett. 34 (1993) 4819
88. Copp B.R., Ireland C.M., and Barrows L.R. J. Org. Chem. 56 (1991) 4596
89. Kinnel R.B., and Scheuer P.J. J. Org. Chem. 57 (1992) 6327
90. Roeca. P., Marsais F., Godard A., Queguiner G., Adams L., and Alo B. Tetrahedron Lett. 36 (1995) 7085
91. Rinehart K.L., Kobayashi J., Harbour G.C., Gilmour J., Mascal M., Holt T.G., Shield L.S., and LaFargue F. J. Amer. Chem. Soc. 109 (1987) 3378
92. McNulty J., and Still I.W.J. Tetrahedron Lett. 32 (1991) 4875
93. Van W.B.C., and Cardellina J.H. Tetrahedron Lett. 30 (1989) 3605
94. Wasserman H.H., and Kellt T.A. Tetrahedron Lett. 30 (1989) 7117
95. Badre A., Boulanger A., Abou-Mansour E., Banaigs B., Combaut G., and Francisco C. J. Nat. Prod. 57 (1994) 528
96. Kobayashi J., Cheng J.-f., Ohta T., Nozoe S., Ohizumi Y., and Sasaki T. J. Org. Chem. 55 (1990) 3666
97. Kobayashi J., Cheng J.-f., Ishibashi M., Nakamura H., Ohizumi Y., Hirata Y., Ohta T., Nozoe S., and Sasaki T. Tennen Yuld Kagobutsu Toronkai 31 (1989) 348
98. Marata O., Shigemon H., Ishibashi M., Sugama K., Hayashi K., and Kobayashi J. Tetrahedron Lett. 32 (1991) 3539
99. Kinzer K.F., and Cardellina J.H. Tetrahedron Lett. 28 (1987) 925
100. Adesanya S.A., Chbani M., Pais M., and Debitus C. J. Nat. Prod. 55 (1992) 525
101. Still I.W.J., and McNulty J. Heterocycles 29 (1989) 2057
102. MeNulty J., and Still I.W.J. J. Chem. Soc. Perkin Trans. 1 (1994) 1329
103. Braeher F., Hildebrand D., and Ernst L. Arch. Pharm., (Weinheim Ger.) 327 (1994) 121
104. Rocca P., Marsais F., Godard A., Queguiner G., Adams L., and Alo B. Synth.Commun. 25 (1995) 3373
105. Molina P., Fresneda P.M., and Garcia-Zafra S. Tetrahedron Lett. 36 (1995) 3581
106. Chbani M., Pais M., Delaunaux J.-M., and Debitus C. J. Nat. Prod. 56 (1993) 105
107. Blunt J.W., Lake R.J., Munro M.H.G., and Toyokuni T. Tetrahedron Lett. 28 (1987) 1825
108. Lake R.J., McCombs J.D., Blunt J.W., Munro M.H.G., and Robinson W.T. Tetrahedron Lett. 29 (1988) 4971
109. Lui J.-J., Nakagawa M., Harada N., Tsuruoka A., Hasegawa A., Ma J., and Hino T. Heterocycles 31 (1990) 229
110. Nakagawa M., Lui J., and Hino T. J. Am. Chem. Soc. 111 (1989) 2721
111. Still I.W.J., and Strautmanis J.R. Tetrahedron Lett. 30 (1989) 1041
112. Still I.W.J., and Strautmanis J.R. Can. J. Chem. 68 (1990) 1408
113. Hermkens H.H., v. Maarseveen J.H., Ottenheijm H.C.J., Kruse C.G., and Scheeren H.W. J. Org. Chem. 55 (1990) 3998
114. Massiot G., Nazabadioko S., and Bliard C. J. Nat. Prod. 58 (1995) 1636
115. Kang H., and Fenical W. Nat. Prod. Lett. 9 (1996) 7
116. Nakamura H., Ohizumi Y., and Hirata Y. Tetrahedron Lett. 27 (1986) 1191
117. Shen G.C., and Baker B.J. Tetrahedron Lett. 35 (1994) 1141
118. Shen G.C., and Baker B.J. Tetrahedron Lett. 35 (1994) 4923
119. Lake R.J., Blunt J.W., and Munro M.H.G. Aust. J. Chem. 42 (1989) 1201
120. Kobayashi J., Harbour G.C., Gilmour J., and Rinehart K.L. J. Am. Chem. Soc. 106 (1984) 1526
121. Hudson J.B., Saboune H., Abramowski Z., Towers G.H.N., and Rinehart K.L. Photochem. Photobiology 47 (1981) 377
122. Nakamura Y., Kobayasi J., Gilmore J., Mascal M., Rinehart K.L., Nakamura H., and Ohizumi Y. J. Biol. Chem. 261 (1986) 4139
123. Kobayasi J., Ishibashi M., Nagai U., and Ohizumi Y. Experientia 45 (1989) 782
124. Molina P., Fresneda P.M., and Gareia-Zafra S. Tetrahedron Lett. 37 (1996) 9353
125. Rinehart K.L., Kobayashi J., Harbour G.C., Hughes R.G., Mizsak S.A., and Scahill T.A. J. Am. Chem. Soc. 106 (1984) 1524
126. Lake R.J., Brennan M.M., Blunt J.W., Munro M.H.G., and Pannell L.K. Tetrahedron Lett. 29 (1988) 2255
127. deSilva D.E., Miao S., Schultz L.W., and Clardy J. Tetrahedron Lett. 33 (1992) 2917
128. Molinski T.F. Chem. Rev. 93 (1993) 1825
129. Kim J., Pordesimo E.O., Toth S.I., Schmitz F.J., and van Altena I. J. Nat. Prod. 56 (1993) 1813
130. Kobayasi J., Cheng J.-f., Walchli M.R., Nakamura H., Hirata Y., Sasaki T., and Ohizumi Y. J. Org. Chem. 53 (1988) 1800
131. Kobayasi J., Tsuda M., Tanabe A., Ishibashi M., Cheng J.-f., Yamamura S., and Sasaki T. J. Nat. Prod. 54 (1991) 1634
132. McDonald L.A., Eldredge G.S., Barrows L.R., and Ireland C.M. J. Med. Chem. 37 (1994) 3819
133. Charyulu G.A., McKee T.C., and Ireland C.M. Tetrahedron Lett. 30 (1989) 4201
134. Rudi A., Benayahu Y., Goldberg I., and Kashman Y. Tetrahedron Lett. 29 (1988) 3861
135. Rudi A. and Kashman Y. 54 (1989) 5331
136. Molinski T.F. and Ireland C.M. 54 (1989) 4256
137. Kobayasi J., Cheng J.-f., Ishibashi M., Nakamura H., Ohizumi Y., Hirata Y., Walchli M.R., and Sasaki T. Tennen Yuki Kagobutsu Toronkai 30 (1988) 268
138. Ciufolini M.A., and Shen Y.C. Tetrahedron Lett. 36 (1995) 4709
139. Ciufolini M.A., and Bryne N.E. J. Am. Chem. Soc. 113 (1991) 8016
140. Szezepankiewiez B.G., and Heathcock C.H. J. Org. Chem. 59 (1994) 3512
141. Ciufolini M.A., Shen Y.C., and Bishop M.J. J. Am. Chem. Soc. 117 (1995) 12460
142. Dunn S.H., and McKillop A. J. Chem. Soc. Perkin Trans. 1 (1993) 879
143. Gellerman G., Rudi A., and Kashman Y. Tetrahedron Lett. 34 (1993) 1823
144. Einat M., Nagler A., Lishner M., Amiel A., Yarkoni S., Rudi A., Gellerman G., Kashman Y., and Fabian I. Clin. Cancer Res. 1 (1995) 823
145. Schmitz F.J., De Guzman F.S., Hossain M.B., and van der Helm D. J. Org. Chem. 56 (1991) 804
146. Cooray N.M., Scheuer P.J., Parkanyi L., and Clardy J. J. Org. Chem. 53 (1988) 4619
147. Carroll A.R., Cooray N.M., Poiner A., and Scheuer P.J. J. Org. Chem. 54 (1989) 4231
148. Carroll A.R., and Scheuer P.J. J. Org. Chem. 55 (1990) 4426
149. Gunawardana G.P., Kohmoto S., and Burres N.S. Tetrahedron Lett. 30 (1989) 4359
150. Steffan B., Brix K., and Putz W. Tetrahedron 49 (1993) 6223
151. Kobayasi J., Cheng J.-f., Nakamura H., Ohizumi Y., Hirata Y., Sasaki T., Ohta T., and Nozoe S. Tetrahedron Lett. 29 (1988) 1177
152. Gunawardana G.P., Koehn F.E., Lee A.Y., Clardy J., He H.Y., and Faulkner D.J. J. Org. Chem. 57 (1992) 1523
153. He H.Y., and Faulkner D.J. J. Org. Chem. 56 (1991) 5369
154. Bloor S.J., and Schmitz F.J. J. Am. Chem. Soc. 109 (1987) 6134
155. De Guzman F.S., and Schmitz F.J. Tetrahedron Lett. 30 (1989) 1069
156. Braeher F. Liebigs Ann. Chem. (1990) 205
157. Schmitz F.J., Agarwal S.K., Gunasekera S.P., Schmidt P.G., and Schoolery J.M. J. Am. Chem. Soc. 105 (1983) 4835
158. Bontemps N., Bonnard I., Banaigs B., Combaut G., and Francisco C. Tetrahedron Lett. 38 (1994) 7023
159. Bonnard I., Bontemps N., Lahmy S., Banaigs B., Combaut G., Francisco C., Colson P., Houssier C., Waring M.J., and Bailly C. Anti-Cancer Drug Des. 10 (1995) 333
160. Echavarren A.M., and Stille J.K. J. Am. Chem. Soc. 110 (1988) 4051
161. Kubo A., and Nakahara S. Heterocycles 27 (1988) 2095
162. Prager R.H., Tsopelas C., and Heisler T. Aust. J. Chem. 44 (1991) 277
163. Prager R.H., Tsopelas C., and Heisler T. Heterocycles 29 (1989) 847
164. Bracher F., and Papke T. Liebigs Ann. Chem. (1996) 115
165. Nakahara S., Tanaka Y., and Kubo A. Heterocycles 43 (1996) 2113
166. Schmitz F.J., De Guzman F.S., Choi Y.-H., Hossain M.B., Rizvi S.K., and van der Helm D. Pure Appl. Chem. 62 (1990) 1393
167. Pitts T.P., Gunawardana G.P., Kelly-Borges M., and Pomponi S. J. Nat. Prod. 55 (1992) 1664
168. Bontemps N., Delforme E., Bastide J., Francisco C., and Bracher F. Tetrahedron 53 (1997) 1743
169. Kitahara Y., Tamura F., and Kubo A. Chem. Pharm. Bull. 42 (1994) 1363
170. Rudi A., Benayahu Y., Goldberg I., and Kashman Y. Tetrahedron Lett. 29 (1988) 6655
171. Shochet N.R., Rudi A., Kashman Y., Hod Y., EI-Maghrabi M.R., and Spector I. J. Cell Physiol. 157 (1993) 481
172. Lindquist N., and Fenical W. Tetrahedron Lett. 31 (1990) 2389