Total synthesis of quinocarcin and its related compounds

Studies in Natural Products Chemistry

Volumn 19, Issue C, 1996, Pages 289-350

  Katoh, Tadashi ^a   Terashima, Shiro ^a  

^a SAGAMI CHEMICAL RESEARCH CENTER   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77957088561     PISSN: 15725995     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S1572-5995(96)80009-3     Document Type: Article

References (103)

1. J. Synth. Org. Chem. Jpn 52 (1994) 556
2. For a recent review on the synthesis of isoquinoline antibiotics, see. Kubo A., and Saito N. Studies in Natural Products Chemistry (1992), Elsevier, Amsterdam 77
3. Tomita F., Takahashi K., and Shimizu K. J. Antibiot. 36 (1983) 463
4. Takahashi K., and Tomita F. J. Antibiot. 36 (1983) 468
5. Tomita F., Takahashi K., and Tamaoki T. J. Antibiot. 37 (1984) 1268
6. Jett J.R., Saijo N., Hong W.-S., Sasaki Y., Takahashi H., Nakano H., Nakagawa K., Sakurai M., Suemasu K., and Terada M. Investigational New Drugs 5 (1987) 155
7. Chiang C.-D., Kanazawa F., Matsushima Y., Nakano H., Nakagawa K., Takahashi H., Terada M., Morinaga S., Tsuchiya R., Sasaki Y., and Saijo N. J. Pharmacobio-Dyn. 10 (1987) 431
8. Fujimoto K., Oka T., and Morimoto M. Cancer Res. 47 (1987) 1516
9. Inaba S., and Shimoyama M. Cancer Res. 48 (1988) 6029
10. Kanamaru R., Konishi Y., Ishioka C., Kakuta H., Sato T., Ishikawa A., Asamura M., and Wakuri A. Cancer Chemother. Pharmacol. 22 (1988) 97
11. Saito H., and Hirata T. Tetrahedron Lett. 28 (1987) 4065
12. Saito H., Kobayashi S., Uosaki Y., Sato A., Fujimoto K., Miyoshi K., Morimoto M., and Hirata T. Chem. Pharm. Bull. 38 (1990) 1278
13. Saito H., Sato A., Ashizawa T., Morimoto M., and Hirata T. Chem. Pharm. Bull. 38 (1990) 3202
14. Williams R.M., Glinka T., Flanangan M.E., Gallegos R., Coffman H., and Pei D. J. Am. Chem. Soc. 114 (1992) 733
15. Williams R.M., Glinka T., Gallegos R., Ehrlich P.P., Flanangan M.E., Coffman H., and Park G. Tetrahedron 47 (1991) 2629
16. Hirayama N., and Shirahata K. J. Chem. Soc. Perkin Trans. 2 (1983) 1705
17. Hill G.C., Wunz T.P., and Remers W.A. J. Comput-Aided Mol. Des. 2 (1988) 91
18. Garner P., Ho W.B., and Shin H. J. Am. Chem. Soc. 114 (1992) 2767
19. Garner P., Ho W.B., and Shin H. J. Am. Chem. Soc. 115 (1993) 10742
20. Sato T., Hirayama F., and Saito T. J. Antibiot. 44 (1991) 1367
21. Suzuki K., Sato T., Morioka M., Nagai K., Abe K., Yamaguchi H., Saito T., Ohmi Y., and Suaki K. J. Antibiot. 44 (1991) 479
22. Katoh T., Kirihara M., Nagata Y., Kobayashi Y., Arai K., Minami J., and Terashima S. Tetrahedron 50 (1994) 6239
23. Katoh T., Kirihara M., Nagata Y., Kobayashi Y., Arai K., Minami J., and Terashima S. Tetrahedron Lett. 34 (1993) 5747
24. Katoh T., and Terashima S. Pure & Appl. Chem. 68 (1996) 703
25. Katoh T., Kirihara M., Yoshino T., Tamura O., Ikeuchi F., Nakatani K., Matsuda F., Yamada K., Gomi K., Ashizawa T., and Terashima S. Tetrahedron 50 (1994) 6259
26. Katoh T., Kirihara M., Yoshino T., and Terashima S. Tetrahedron Lett. 34 (1993) 5751
27. Danishefsky S.J., Harison P.j., Webb II R.R., and O'Neill B.T. J. Am. Chem. Soc. 107 (1985) 1421
28. Fukuyama T., and Nunes J.J. J. Am. Chem. Soc. 110 (1988) 5196
29. Flanagan M.E., and Williams R.M. J. Org. Chem. 60 (1995) 6791
30. and references cited therein. Danishefsky S.J., Uang B.-J., and Quallich G. J. Am. Chem. Soc. 106 (1984) 2453
31. Nicolaou K.C., Claremon D.A., Barnette W.E., and Seitz S.P. J. Am. Chem. Soc. 101 (1979) 3704
32. The Z isomer of 18 did not undergo appreciable cycization under these conditions. It is recovered upon chromatographic purification of the crude t afforded a ca. 7:1 mixture of the desired exo-olefin and its endo-olefinic isomer
33. Danishefsky S.J., O'Neill B.T., Taniyama E., and Vaughan K. Tetrahedron Lett. 25 (1984) 4199
34. Diago-Meseguer J., Paloma-Coll A.L., Fernández-Lizarbe J.R., and Zugaza-Bilbao A. Synthesis (1980) 547
35. Danishefsky S.J., O'Neill B.T., and Springer J.P. Tetrahedron Lett. 25 (1984) 4203
36. The end-methoxycarbonyl isomer was also obtained in 10% yield
37. Burgess E.M., Penton Jr. H.R., and Taylor E.A. J. Org. Chem. 38 (1973) 26
38. Kiss M., Russel-Maynard J., and Joule J.A. Tetrahedron Lett. 28 (1987) 2187
39. Allway P.A., Sutherland J.K., and Joule J.A. Tetrahedron Lett. 33 (1990) 4781
40. Peters D.A., Beddoes R.L., and Joule J.A. J. Chem. Soc. Perkin Trans. 1 (1993) 1217
41. Garner P., Sunitha K., and Shanthilal T. Tetrahedron Lett. 29 (1988) 3525
42. Garner P., Sunitha K., Ho W.B., Youngs W.J., Kennedy V.O., and Djebli A. J. Org. Chem. 54 (1989) 2041
43. Garner P., Arya F., and Ho W.B. J. Org. Chem. 55 (1990) 3937
44. Garner P., Ho W.B., Grandhee S.K., Youngs W.J., and Kennedy V.O. J. Org. Chem. 56 (1991) 5893
45. Williams R.M., Ehrlich P.P., Zhai W., and Hendrix J. J. Org. Chem. 52 (1987) 2615
46. Fuji K., Ichikawa K., Node M., and Fujita E. J. Org. Chem. 44 (1979) 1661
47. Hauser F.M., and Ellenberger S.R. Synthesis (1987) 723
48. Ogura K., Ito Y., and Tuchihashi G. Bull. Chem. Soc. Jpn. 52 (1979) 2013
49. Evans D.A., Britton T.C., Ellman J.A., and Dorow R.L. J. Am. Chem. Soc. 112 (1990) 4011
50. Scheiner P. J. Org. Chem. 30 (1965) 7
51. Vandewalle M., Van der Eycken J., Oppolzer W., and Vullioud C. Tetrahedron 42 (1986) 4035
52. Thom C., and Kocienski P. Synthesis (1992) 582
53. Kim B.H., and Curran D.P. Tetrahedron 49 (1993) 293
54. Saito S., Tamura O., Kobayashi Y., Matsuda F., Katoh T., and Terashima S. Tetrahedron 50 (1994) 6193
55. Saito S., Matsuda F., and Terashima S. Tetrahedron Lett. 29 (1988) 6301
56. Saito S., Tanaka K., Nakatani K., Matsuda F., Katoh T., and Terashima S. Tetrahedron 50 (1994) 6209
57. Saito S., Tanaka K., Nakatani K., Matsuda F., and Terashima S. Tetrahedron Lett. 30 (1989) 7423
58. Katoh T., Kirihara M., Nagata Y., Kobayashi Y., Arai K., Minami J., and Terashima S. Tetrahedron 50 (1994) 6239
59. Katoh T., Kirihara M., Nagata Y., Kobayashi Y., Arai K., Minami J., and Terashima S. Tetrahedron Lett. 34 (1993) 5747
60. Katoh T., Nagata Y., Kobayashi Y., Arai K., Minami J., and Terashima S. Tetrahedron 50 (1994) 6221
61. Katoh T., Nagata Y., Kobayashi Y., Arai K., Minami J., and Terashima S. Tetrahedron Lett. 34 (1993) 5743
62. Quitt P., Hellerbach J., and Vogel K. Helv. Chim. Acta 46 (1963) 327
63. Silverman R., and Levy M.A. J. Org. Chem. 45 (1980) 815
64. Hamada Y., and Shioiri T. Chem. Pharm. Bull. 30 (1982) 1921
65. Flynn D.L., Zelle R.E., and Grieco P.A. J. Org. Chem. 48 (1983) 2424
66. Bredereck H., Simchen G., Rebsdat S., Kantlehner W., Horn P., Wahl R., Hoffmann H., and Grieshaber P. Chem. Ber. 101 (1968) 41
67. Corey E.J., Yuen P.-W., Hannon F.J., and Wierda D.A. J. Org. Chem. 55 (1990) 784
68. Langlois N., and Rojas A. Tetrahedron 49 (1993) 77
69. Asher V., Becu C., Anteunis M.J.O., and Callens R. Tetrahedron Lett. 22 (1981) 141
70. Irie K., Aoe K., Tanaka T., and Saito S. J. Chem. Soc., Chem. Commun. (1985) 633
71. Thaning M., and Wistrand L.-G. Acta Chem. Scand. 43 (1989) 290
72. Inoue S., Saito K., Kato S., Nozaki S., and Sato K. J. Chem. Soc, Perkin Trans. 1 (1974) 2097
73. Mukaiyama T., Suzuki K., and Yamada T. Chem. Lett. (1982) 929
74. Gschwend H.W., and Rodriguez H.R. Org. Reactions (1979) 26
75. Carpenter T.A., Evans G.E., Leeper F.J., Staunton J., and Wilkinson M.R. J. Chem. Soc. Perkin Trans. 1 (1984) 1043
76. Watanabe M., Sahara M., Furukawa S., Billedeau R., and Snieckus V. Tetrahedron Lett. 23 (1982) 1647
77. Broka C.A. Tetrahedron Lett. 32 (1991) 859
78. Borch R.F., Bernstein M.D., and Dursr H.D. J. Am. Chem. Soc. 93 (1971) 2897
79. Rosini G., Medici A., and Soverini M. Synthesis (1979) 789
80. Chiba T., Ishizawa T., Sakai J., and Kaneko C. Chem. Pharm. Bull. 35 (1987) 4672
81. Natarajan S., and Pai B.R. Ind. J. Chem. 12 (1974) 355
82. Bichaut P., Thuiller G., and Rumpf P. C. R. Hebd. Seances Acad. Sci. Ser. C 269 (1969) 1550
83. Ishida A., Fujii H., Nakamura T., Ohishi T., Aoe E., Nishibata Y., and Kinumaki A. Chem. Pharm. Bull. 34 (1986) 1994
84. Polniaszek R.P., and Belmont S.E. J. Org. Chem. 55 (1990) 4688
85. Windholz T.B., and Johnston D.B.R. Tetrahedron Lett. 27 (1967) 2555
86. Kim K.S., Song Y.H., Lee B.H., and Hahn C.S. J. Org. Chem. 51 (1986) 404
87. Weinstein B., Watrin K.G., Loie H.J., and Martin J.C. J. Org. Chem. 41 (1976) 3634
88. Yamada S., and Kunieda T. Chem, Pharm. Bull. (1967) 491
89. Lessen T.A., Demko D.M., and Weinreb S.M. Tetrahedron Lett. 31 (1990) 2105
90. Rawal V.H., Rao J.A., and Cave M.P. Tetrahedron Lett. 26 (1985) 4275
91. Gibian H., and Klieger E. Liebig's Ann. Chem. 640 (1961) 145
92. For a recent rewiew of intramolecular N-acyliminium ion cyclizations, see. Hiemstra H., and Speckamp W.N. The Alkaloids. In: Brossi A. (Ed) (1988), Academic Press, New York 271
93. Saito H., Hirata T., Kasai M., Fujimoto K., Ashizawa T., Morimoto M., and Sato A. J. Med. Chem. 34 (1991) 1959
94. Zimmer H., Lankin D.C., and Horgan S.W. Chem. Rev. 71 (1971) 229
95. Dale J.A., Dull D.L., and Mosher H.S. J. Org. Chem. 34 (1969) 2543
96. Takai K., Hotta Y., Oshima K., and Nozaki H. Tetrahedron Lett. (1978) 2417
97. Corey E.J., and Winter P.A.E. J. Am. Chem. Soc. 85 (1963) 2677
98. Nagaoka H., Miyakoshi T., Kasuga J., and Yamada Y. Tetrahedron Lett. 26 (1985) 5053
99. 1H-NMR spectrum of 159 exhibited a signal due to the C-4 proton as a separated broad triplet (J = 3.5 Hz) at δ = 4.24
100. Barton D.H.R., Crich D., and Motherwell W.B. Chem. Soc. Chem. Commun. (1983) 939
101. Barton D.H.R., Crich D., and Motherwell W.B. Tetrahedron 43 (1987) 4321
102. Barton D.H.R. Aldrichimica Acta 23 (1990) 3
103. Personal communication from Dr. T. Hirata, Kyowa Hakko Kogyo Co., Ltd.