Total synthesis of naphthylisoquinoline alkaloids

Studies in Natural Products Chemistry

Volumn 20, Issue PART F, 1997, Pages 407-455

  Rizzacasa, Mark A ^a  

^a UNIVERSITY OF MELBOURNE   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77957116008     PISSN: 15725995     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S1572-5995(97)80035-X     Document Type: Article

References (96)

1. Bringmann G., and Pokorny F. The Alkaloids. In: Cordell G. (Ed) (1995), Academic Press, New York 127-271
2. Govindachari T.R., and Parthasarathy P.C. Tetrahedron 27 (1971) 1013
3. Chen Z.X., Wang B.D., Quin K.W., Zhang B.E., Su Q.L., and Lin Q.C. Yaoxue Xuebao 16 (1981) 519
4. Bringmann G., and Kinzinger L. Phytochemistry 31 (1992) 3297
5. Govindachari T.R., Parthasarathy P.C., and Desai H.K. Indian J. Chem. 10 (1972) 1117
6. Govindachari T.R., Parthasarathy P.C., Rajagolpalan T.G., Desai H.K., Ramachandran K.S., and Lee E. J. Chem. Soc., Perkin Trans. 1 (1975) 2134
7. Govindachari T.R., Parthasarathy P.C., and Desai H.K. Indian J. Chem. 11 (1973) 1190
8. Manfredi K.P., Blunt J.W., Cardellina II J.H., McMahon J.B., Pannel L.L., Cragg G.M., and Boyd M.R. J. Med. Chem. 34 (1991) 3402
9. Bringmann G., Zagst R., Schäiffer M., Hallock Y.F., Cardellina II J.H., and Boyd M.R. Angew. Chem. Int. Ed. Engl. 32 (1993) 1190
10. Boyd M.R., Hallock Y.F., Cardellina II J.H., Manfredi K.P., Blunt J.W., McMahon J.B., Buckheit R.W., Bringmann G., Schäffer M., Cragg G.M., Thomas D.W., and Jato J.G. J. Med. Chem. 37 (1994) 1740
11. Bruncton J., Bouquet A., Fornet A., and Cavé A. Phytochemistry 15 (1976) 817
12. Bringmann G., Rübenacker M., Weirich R., and Assi L.A. Phytochemistry 31 (1992) 4019
13. Bringmann G. Angew. Chem. Int. Ed. Engl. 21 (1982) 200
14. Bringmann G. Tetrahedron Lett. 23 (1982) 2009
15. Bringmann G., and Jansen J.R. Heterocycles 24 (1986) 2407
16. For a review on biaryl synthesis see. Bringmann G., Walter R., and Weirich R. Angew. Chem., Int. Ed. Engl. 29 (1990) 977
17. For a review on the chemistry of 2-oxazolines see. Meyers A.I., and Gant T.G. Tetrahedron (1994) 2297
18. Meyers A.I., and Lutomski K.A. J. Am. Chem. Soc. 104 (1982) 879
19. Meyers A.I., and Himmelsbach R.J. J. Am. Chem. Soc. 107 (1985) 682
20. Meyers A.I., and Moorlag H. Tetrahedron Lett. 34 (1993) 6989
21. Rizzacasa M.A., and Sargent M.V. J. Chem. Soc., Perkin Trans. 1 (1991) 2773
22. Wilson J.M., and Cram D.J. J. Am. Chem. Soc. 104 (1982) 881
23. Hattori T., Koike N., and Miyano S. J. Chem. Soc., Perkin Trans. 1 (1994) 2273
24. Baker R.W., Pocock G.R., Sargent M.V., and Twiss E. Tetrahedron Asymmetry 4 (1993) 2423
25. Uemura M., Watanbe T., and Kamikawa K. J. Org. Chem. 61 (1996) 1375
26. Meyers A.I., and Warshawsky A.M. J. Am. Chem. Soc. 112 (1990) 8090
27. Knight D.W. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis: Selectivity, Strategy and Efficiency in Modern Organic Chemistry (1991), Pergamon Press, Oxford, England, New York 481
28. Kamikawa K., Watanabe T., and Uemura M. Synlett (1995) 1040
29. Shindo M., Koga K., and Tomioka K. J. Am. Chem. Soc. 114 (1992) 8732
30. Hayashi T., Hayashizaki K., Kiyoi T., and Ito Y. J. Am. Chem. Soc. 110 (1988) 8153
31. Whiting D.A. Comprehensive Organic Synthesis: Selectivity, Strategy and Efficiency in Modern Organic Chemistry. In: Trost B.M., and Fleming I. (Eds) (1991), Pergamon Press, Oxford, England, New York 659
32. Tanaka M., Mitsuhashi H., and Wakamatsu T. Tetrahedron Lett. 33 (1992) 4164
33. Evans D.A., Dinsmore C.J., Evrard D.A., and De Vries K.M. J. Am. Chem. Soc. 115 (1993) 6426
34. Bringmann G., and Jansen J.R. Heterocycles 28 (1989) 137
35. Bringmann G., and Reuscher H. Tetrahedron Lett. 30 (1989) 5249
36. Bringmann G., Hartung T., Göbel L., Schupp O., Ewers C.L.J., Schöner B., Zagst R., Peters K., G.von Schnering H., and Burschka C. Liebigs Ann. Chem. (1992) 225
37. Bringmann G., Hartung T., Göbel L., Schupp O., Peters K., and von Schnering H.G. Liebigs Ann. Chem. (1992) 769
38. Bringmann G., and Hartung T. Angew. Chem., Int. Ed. Engl. 31 (1992) 761
39. Bringmann G., and Hartung T. Tetrahedron 49 (1993) 7891
40. Corey E.J., Bakshi R.K., and Shibata S. J. Am. Chem. Soc. 109 (1987) 5551
41. Bringmann G., and Vitt D. J. Org. Chem. 60 (1995) 7674
42. Bringmann G., Walter R., and Ewers C.L.J. Synlett (1991) 581
43. Bringmann G., and Reuscher H. Angew. Chem., Int. Ed. Engl. 28 (1989) 1672
44. Lavault M., and Bruneton J. C. R. Seances Acad. Sci. (Paris) C287 (1978) 129
45. Bringmann G., and Jansen J.R. Tetrahedron Lett. 25 (1984) 2537
46. Fanta P.E. Synthesis (1974) 9
47. Bringmann G. The Alkaloids. In: Cordell G. (Ed) (1986), Academic Press, New York 141-184
48. Bringmann G., Jansen J.R., and Rink H.-P. Angew. Chem., Int. Ed. Engl. 25 (1986) 913
49. Rizzacasa M.A., and Sargent M.V. J. Chem. Soc., Chem. Commun. (1989) 301
50. Rizzacasa M.A., and Sargent M.V. J. Chem. Soc., Perkin Trans. 1 (1991) 841
51. Heinzman S., and Grunwell J. Tetrahedron Lett. 21 (1980) 4305
52. Jung M.E., and Hagenah J.A. J. Org. Chem. 52 (1987) 1889
53. Findlay J.A., Daljeet A., Murray P.J., and Rej R.N. Can. J. Chem. 65 (1987) 427
54. Nichols D.E., Bartknecht C.F., and Rusterholz D.B. J. Med. Chem. 16 (1973) 480
55. Bringmann G., Weirich R., Reuscher H., Jansen J.R., Kinzinger L., and Ortmann T. Leibigs Ann. Chem. (1993) 877
56. Maruoka K., and Yamamoto H. Angew. Chem., Int. Ed. Engl. 24 (1985) 668
57. Brossi A., and Teitel S. Helv. Chim. Acta 53 (1970) 1179
58. Bringmann G., and Jansen J.R. Heterocycles 28 (1989) 137
59. Bringmann G., Kinzinger L., Busse H., and Zhao C. Planta Med. 58 (1992) 704
60. Rizzacasa M.A., and Sargent M.V. J. Chem. Soc., Chem. Commun. (1990) 894
61. Rizzacasa M.A., and Sargent M.V. J. Chem. Soc., Perkin Trans. 1 (1991) 845
62. Meyers A.I., Knaus G., Kamata K., and Ford M.E. J. Am. Chem. Soc. 98 (1976) 567
63. Hall D.M., Ridgwell S., and Turner E.E. J. Chem. Soc. (1954) 2498
64. Kuhn R., and Albrecht O. Liebigs Ann. Chem. 465 (1928) 282
65. Stanley W.M., McMahon E., and Adams R. J. Am. Chem. Soc. 55 (1933) 706
66. Johnson C.R., Elliott R.C., and Penning T.D. J. Am. Chem. Soc. 106 (1984) 5019
67. Cooper D.B., Hall C.R., harrison J.M., and Inch T.D. J. Chem. Soc., Perkin Trans. 1 (1977) 1969
68. Helmchen G., and Nill G. Angew. Chem., Int. Ed. Engl. 18 (1979) 65
69. Helmchen G., Nill G., Flockerzi D., Schühle W., and Youssef M.S.K. Angew. Chem., Int. Ed. Engl. 18 (1979) 64
70. Helmchen G., Nill G., Flockerzi D., and Youssef M.S.K. Angew. Chem., Int. Ed. Engl. 18 (1979) 63
71. Bringmann G., Zagst R., Reuscher H., and Aké Assi L. Phytochemistry 31 (1992) 4011
72. Rizzacasa M.A., and Sargent M.V. J. Chem. Soc., Chem. Commun. (1991) 278
73. Leighton B.L., and Rizzacasa M.A. J. Org. Chem. 60 (1995) 5702
74. Gable R.W., Martin R.L., and Rizzacasa M.A. Aust. J. Chem. 48 (1995) 2013
75. Chau P., R.Czuba I., Rizzacasa M.A., Bringmann G., Gulden K.-P., and Schäffer M. J. Org. Chem. 61 (1996) 7101
76. Foucher J.-P., Pousset J.-L., Cáve A., and Cáve A. Phytochemistry 13 (1974) 1253
77. Bringmann G., Jansen J.R., Reuscher H., Rübenacker M., Peters K., and von Schnering G. Tetrahedron Lett. 31 (1990) 643
78. Bringmann G., and Jansen J.R. Synthesis (1991) 825
79. Bringmann G., and Reuscher H. Angew. Chem., Int Ed. Engl. 28 (1989) 1672
80. Manfredi K.P., Blunt J.W., Cardellina II J.H., McMahon J.B., Pannell L.L., Gragg G.M., and Boyd M.R. J. Med. Chem. 34 (1991) 3402
81. Boyd M.R., Hallock Y.F., Cardellina II J.H., Manfredi K.P., Blunt J.W., McMahon J.B., Buckheit Jr. R.W., Bringmann G., Schäffer M., Gragg G.M., Thomas D.W., and Jato J.G. J. Med. Chem. 37 (1994) 1740
82. Hallock Y.F., Manfredi K.P., Blunt J.W., Cardellina II J.H., Schäffer M., Gulden K.-P., Bringmann G., Lee A.Y., Clardy J., Francois G., and Boyd M. J. Org. Chem. 59 (1994) 6349
83. Bringmann G., Harmsen S., Holenz J., Geuder T., Götz R., Keller P.A., Walter R., Hallock Y.F., Cardellina II J.H., and Boyd M.R. Tetrahedron 50 (1994) 9643
84. Bringmann G., Götz R., Keller P.A., Walter R., Henschel P., Schäffer M., Stäblein M., Kelly T.R., and Boyd M.R. Heterocycles 39 (1994) 503
85. For a review see. Stille J.K. Angew. Chem., Int. Ed. Engl. 25 (1986) 508
86. Rizzacasa M.A., and Sargent M.V. Aust. J. Chem. 40 (1987) 1737
87. Owton W.M., Gallagher P.T., and Juan-Montesinos A. Synthetic Commun. 23 (1993) 2119
88. Laatsch H. Liebigs Ann. Chem. (1980) 1321
89. Kelly T.R., Garcia A., Lang F., Walsh J.J., Bhasker K.V., Boyd M.R., Götz R., Keller P.A., Walter R., and Bringmann G. Tetrahedron Lett. 35 (1994) 7621
90. Miraura N., and Suzuki A. Chem. Rev. 95 (1995) 2457
91. Hoye T.R., Chen M., Mi L., and Priest O.P. Tetrahedron Lett. 35 (1994) 8747
92. Hoye T.R., and Mi L. Tetrahedron Lett. 37 (1996) 3097
93. Bringmann G., Zagst R., Reusher H., and Assi L.A. Phytochemistry 31 (1992) 2011
94. Hoye T.R., and Chen M. Tetrahedron Lett. 37 (1996) 3099
95. Rama Rao A.V., Gunjar M.K., Ramana D.V., and Chheda A.K. Heterocycles 43 (1996) 1
96. Hobbs P.D., Upender V., Liu J., Pollart D.J., Thomas D.W., and Dawson M.I. J. Chem. Soc., Chem. Commun. (1996) 923