The dolastatins; 18: Stereospecific synthesis of dolaproine

Synthesis

Volumn , Issue 6, 1996, Pages 719-725

  Pettit, George R ^a   Burkett, Douglas D ^a   Barkóczy, József ^a   Breneman, Gary L ^b   Pettit, William E ^a  

^a ARIZONA STATE UNIVERSITY   (United States)

^b EASTERN WASHINGTON UNIVERSITY   (United States)

Author keywords

antineoplastic peptide; chiral oxazolidinone; dolastatin 10; stereospecific aldol reaction

Indexed keywords

ANTINEOPLASTIC AGENT; DOLAPROINE; DOLASTATIN 10; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0029813384     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4296     Document Type: Article

References (104)

1. See for parts 17 and 265 in the series the Dolastatins and Antineoplastic Agents: Pettit, G.R.; Singh, S.B.; Herald, D.L.; Lloyd-Williams, P.; Kantoci, D.; Burkett, D.; Barkóczy, J.; Hogan, F.; Wardlaw, T.R. J. Org. Chem. 1994, 59, 6287.
2. Pettit, G.R.; Kamano, Y.; Herald, C.L.; Fujii, Y.; Kizu, H.; Boyd, M.R.; Boettner, F.E.; Doubek, D.L.; Schmidt, J.M.; Chapuis, J.C.; Michel, C. J. Tetrahedron 1993, 49, 9151.
3. (a) Hu, Z.-B.; Gignac, S.M.; Quentmeier, H.; Pettit, G.R.; Drexler, H. Leukemia Res. 1993, 17, 333.
4. (b) Bai, R.; Roach, M.C.; Jayaram, S.K.; Barkóczy, J.; Pettit, G.R.; Ludeña, R.F.; Hamel, E. Biochem. Pharmacol. 1993, 45, 1503.
5. (c) Quentmeier, H.; Brauer, S.; Pettit, G.R.; Drexler, H.G. Leukemia Lymphoma 1992, 6, 245.
6. (d) Beckwith, M.; Urba, W.J.; Longo, D.L. J. Natl. Cancer Inst. 1993, 483.
7. (e) Steube, K.G.; Grunicke, D.; Pietsch, T.; Gignac, S.M.; Pettit, G.R.; Drexler, H.G. Leukemia 1992, 6, 1048.
8. (f) Ludeña, R.F.; Roach, M.C.; Prasad, V.; Pettit, G.R. Biochem. Pharmacol. 1992, 43, 539.
9. (g) Bai, R.; Pettit, G.R.; Hamel, E. J. Biol. Chem. 1990, 265, 17141.
10. Pettit, G.R.; Kamano, Y.; Herald, C.L.; Tuinman, A.A.; Boettner, F.E.; Kizu, H.; Schmidt, J.M.; Baczynskyj, L.; Tomer, K.B.; Bontems, R.J. J. Am. Chem. Soc. 1987, 109, 6883.
11. Pettit, G.R.; Singh, S.B.; Hogan, F.; Lloyd-Williams, P.; Burkett, D.D.; Glewlow, P.J. J. Am. Chem. Soc. 1989, 111, 5463.
12. (a) Evans, D.A.; Rieger, D.L.; Bilodcau, M.T.; Urpi, F. J. Am. Chem. Soc. 1991, 113, 1047.
13. (b) Nerz-Stormes, M.; Thornton, E.R. J. Org. Chem. 1991, 56, 2489.
14. (c) Van Draanen, N.A.; Arseniyadis, S.; Grimmins, M.T.; Heathcock, C.H. J. Org. Chem. 1991, 56, 2499.
15. (d) Inoue, T.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1980, 53, 174.
16. (e) Danda, H.; Hansen, M.M.; Heathcock, C.H. J. Org. Chem. 1990, 55, 173.
17. (f) Pollack, R.M. Tetrahedron 1989, 45, 4913.
18. (g) Paterson, I.; Goodman, J.M. Tetrahedron Lett. 1989, 30, 997.
19. (h) Denmark, S.E.; Henke, B.R. J. Am. Chem. Soc. 1989, 111, 8032.
20. (i) Meyers, A.I.; Yamamoto, Y. Tetrahedron 1984, 40, 2309.
21. (j) Narasaka, K.; Miwa, T. Chem. Lett. 1985, 1217.
22. (k) Li, Y.; Paddon-Row, M.N.; Houk, K.N. J. Org. Chem. 1990, 55, 481.
23. (l) Denmark, S.E.; Henke, B.R. J. Am. Chem. Soc. 1991, 113, 2177.
24. (m) Kleschick, W.A.; Buse, C.T.; Heathcock, C.H. J. Am. Chem. Soc. Chem. Commun. 1977, 99, 247.
25. (n) Furuta, K.; Maruyama, T.; Yamamoto, H.J. Am. Chem. Soc. 1991, 113, 1041.
26. (a) Ito, Y.; Sasaki, A.; Tamoto, K.; Sunagawa, M.; Terashima, S. Tetrahedron 1991, 47, 2801.
27. (b) Basile, T.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Chem. Soc., Chem. Commun. 1989, 596.
28. (c) Tamaru, Y.; Nakamura, T.; Sakaguchi, M.; Ochiai, H.; Yoshida, Z. J. Chem. Soc., Chem. Commun. 1988, 610.
29. (d) Fürstner, A. Synthesis 1989, 571.
30. (e) Ito, Y.; Terashima, S. Tetrahedron Lett. 1987, 28, 6629.
31. (f) Tanaka, K.; Kishigami, S.; Toda, F. J. Org. Chem. 1991, 56, 4333.
32. (g) Araki, S.; Katsumura, N.; Kawasaki, K.I.; Butsugan, Y. J. Chem. Soc., Perkin Trans. 1 1991, 499.
33. (h) Bouhlel, E.; Rathke, M.W. Synth. Commun. 1991, 21, 133.
34. (i) Papadopoulou, M.V. Chem. Ber. 1989, 122, 2017.
35. (j) Perminder, S.J.; Araki, S.; Butsugan, Y. J. Chem. Soc., Perkin Trans. 1, 1992, 711.
36. (a) Longmire, C. F.; Evans, S. A., Jr. J. Chem. Soc., Chem. Commun. 1990, 922.
37. (b) Wei, Y.; Bakthavatchalam, R. Tetrahedron 1991, 32, 1535.
38. (c) Johnson, C.R.; Chen, Y.-F. J. Org. Chem. 1991, 56, 3344.
39. (d) Panyachotipun, C.; Thornton, E.R. Tetrahedron Lett. 1990, 31, 6001.
40. (e) Zoretic, P.A.; Biggers, M.S.; Biggers, G.K.; Caspar, M.L. Synth. Commun. 1991, 21, 31.
41. (f) Mon, I.; Ishihara, K.; Heathcock, C.H. J. Org. Chem. 1990, 55, 1114.
42. (g) Arnett, E.M.; Fisher, F.J.; Nichols, M.A.; Ribiero, A.A. J. Am. Chem. Soc. 1990, 112, 801.
43. (h) Braun, M.; Waldmüller, D. Synthesis 1989, 856.
44. (i) Majewski, M.; Cleave, D.M. Tetrahedron Lett. 1989, 30, 5681.
45. (j) Barr, D.; Berrisford, D.J.; Bones, R.V.H.; Slawin, A.M.Z.; Snaith, R.; Stoddart, F.; Williams, D.J. Angew. Chem., Int. Ed. Engl. 1989, 28, 1044.
46. (k) Arnett, E.M.; Fisher, F.J.; Nichols, M.A.; Ribeiro, A.A. J. Am. Chem. Soc. 1989, 111, 748.
47. Toda, F.; Tanaka, K.; Hamai, K. J. Chem. Soc., Perkin Trans. 1 1990, 3207.
48. Pearson, W.H.; Hines, J.V. J. Org. Chem. 1989, 54, 4235.
49. (a) Evans, D.A.; Clark, J.S.; Metternich, R.; Novak, V.J.; Sheppard, G.S. J. Am. Chem. Soc. 1990, 112, 866.
50. (b) Gennari, C.; Bernardi, A.; Colombo, L.; Scolastico, C. J. Am. Chem. Soc. 1985, 107, 5812.
51. (c) Helmchen, G.; Leikauf, U.; Taufer-Knöpfel, I. Angew. Chem., Int. Ed. Engl. 1985, 24, 874.
52. Yamamoto, Y.; Maruyama, K. Tetrahedron Lett. 1980, 21, 4607.
53. (a) Zhang, Y.; Xu, W. Synth. Commun. 1989, 19, 1291.
54. (b) Mukai, C.; Suzuki, K.; Nagami, K.; Hanaoka, M. J. Chem. Soc., Perkin Trans. 1 1992, 141.
55. Sato, S.; Matsuda, I.; Izumi, Y. Tetrahedron Lett. 1987, 28, 6657.
56. Nokami, J.; Mandai, T.; Watanabe, H.; Ohyama, H.; Tsuji, J. J. Am. Chem. Soc. 1989, 111, 4126.
57. Davies, S.G.; Dordor-Hedgecock, I.M.; Warner, P. Tetrahedron Lett. 1985, 26, 2125.
58. Sawamura, M.; Hamashima, H.; Ito, Y. J. Org. Chem. 1990, 55, 5935.
59. (a) Sawamura, M.; Ito, Y.; Hayashi, T. Tetrahedron Lett. 1990, 31, 2723.
60. (b) Togni, A.; Pastor, S.D. J. Org. Chem. 1990, 55, 1649.
61. (c) Togni, A.; Pastor, S.D.; Rihs, G. Hel. Chim. Acta 1989, 72, 1471.
62. (d) Ito, Y.; Sawamura, M.; Hamashima, H.; Emura, T.; Hayashi, T. Tetrahedron Lett. 1989, 30, 4681.
63. (a) von der Osten, C.H.; Sinskey, A.J.; Barbas, C.F., III; Pederson, R. L.; Wang, Y.-F.; Wong, C.-H. J. Am. Chem. Soc. 1989, 111, 3924.
64. (b) Kitagawa, O.; Taguchi, T.; Kobayashi, Y. Tetrahedron Lett. 1988, 29, 1803.
65. Yamamoto, Y.; Maruyama, K. J. Am. Chem. Soc. 1982, 104, 2323.
66. Myers, A.C.; Widowson, K.L. J. Am. Chem. Soc. 1990, 112, 9672.
67. (a) Curtis, A.D.M.; Whiting, A. Tetrahedron Lett. 1991, 32, 1507.
68. (b) Heathcock, C. H. Aldrichimica Acta 1990, 23, 99.
69. (c) Shimizu, H.; Hara, S.; Suzuki, A. Synth. Commun. 1990, 20, 549.
70. (d) Savrda, J.; Descoins, C. Synth. Commun. 1987, 17, 1901.
71. (e) Jefford, C.W.; Jaggi, D.; Boukouvalas, J. J. Chem. Soc., Chem. Commun. 1988, 1595.
72. (f) Masamune, S.; Sato, T., kim, B.; Wollmann, T.A. J. Am. Chem. Soc. 1986, 108, 8279.
73. Yamamoto, Y.; Hatsuya, S.; Yamada, J.-I. J. Org. Chem. 1990, 55, 3118.
74. (a) Evans, D.A.; Weber, A.E. J. Am. Chem. Soc. 1987, 109, 7151.
75. (b) Fan, R.; Hudlicky, T. Tetrahedron Lett. 1989, 30, 5533.
76. (c) Tomioka, K. Synthesis 1990, 541.
77. (d) Mukaiyama, T.; Uchiro, H.; Kobayashi, S. Chem. Lett 1989, 1001.
78. (a) Zhang, Y.; Liu, T.; Lin, R. Synth. Commun. 1988, 18, 2003
79. (b) Kobayashi, S.; Hachiya, I. Tetrahedron Lett. 1992, 33 1625.
80. Harada, T.; Mukaiyama, T. Chem. Lett. 1982, 467.
81. Evans, D.A.; McGee, L.R. Tetrahedron Lett. 1983, 24, 3975
82. Nakamura, E.; Kuwajima, I. Tetrahedron Lett. 1983, 24, 3303.
83. Gennari, C.; Colombo, L.; Scolastico, C.; Todeschini, R. Tetrahedron 1993, 40, 4051.
84. Mukaiyama, T.; Iwasawa, N.; Stevens, R.W.; Haga, T. Tetrahedron 1984, 40, 1381.
85. Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1985, 26, 587.
86. Labadie, S.S.; Stille, J.K. Tetrahedron 1984, 40, 2329.
87. (a) Evans, D.A.; Mathre, D.J.; Scott, W.L. J. Org. Chem. 1994, 50, 1830.
88. (b) Gage, J.R.; Evans, D.A. Org. Synth. 1989, 68, 83.
89. Evans, D.A.; Bartroli, J.; Shih, T.L. J. Am. Chem. Soc. 1981, 103, 2127.
90. Correa, A.; Denis, J.-N.; Greene, A.E. Synth. Commun. 1991, 21, 1.
91. Kono, S.; Yokomatsu, T.; Shibuya, S. J. Org. Chem. 1989, 54, 515.
92. Walker, M. A.; Heathcock, C.H. J. Org. Chem. 1991, 56, 5747.
93. (a) Hamada, Y.; Shioiri, T. Chem. Pharm. Bull. 1982, 30, 1921.
94. (b) Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1982, 23, 1193.
95. (c) Hamada, Y.; Kohda, K.; Shioiri, T. Tetrahedron Lett. 1984, 25, 5303.
96. (d) Parikh, J.R.; Doering, W. von E. J. Am. Chem. Soc. 1967, 89, 5505.
97. (e) Hamada, Y.; Shibata, M.; Sugiura, T.; Kato, S.; Shioiri, T. J. Org. Chem. 1987, 52, 1252.
98. (a) Hamada, Y.; Hayashi, K.; Shioiri, T. Tetrahedron Lett. 1991, 32, 931.
99. (b) Shioiri, T.; Hayashi, K.; Hamada, Y. Tetrahedron 1993, 49, 1913.
100. Hayashi, K.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1991, 32, 7287.
101. Shimizu, H.; Hara, S.; Suzuki, A. Synth. Commun. 1990, 20, 549.
102. Diem, M.J.; Burow, D.F.; Fry, J.L. J. Org. Chem. 1977, 42, 180.
103. Cromer, D.T.; Mann, J.B. Acta Crystallogr. Sect. A 1968, 24, 321.
104. Enraf-Nonius MoIEN Structure Determination System; Delft, The Netherlands, 1990.