Total synthesis of 16-desmethylepothilone B, epothilone B10, epothilone F, and related side chain modified epothilone B analogues

Chemistry - A European Journal

Volumn 6, Issue 15, 2000, Pages 2783-2800

  Nicolaou, K C ^a,b   Hepworth, David ^a   King, N Paul ^a   Finlay, M Raymond V ^a   Scarpelli, Rita ^a   Pereira, M Manuela A ^a   Bollbuck, Birgit ^a   Bigot, Antony ^a   Werschkun, Barbara ^a   Winssinger, Nicolas ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Antitumor agents; Designed analogues; Epothilone; Synthesis; Total synthesis

Indexed keywords

ANTINEOPLASTIC AGENT; EPOTHILONE A; EPOTHILONE B; EPOTHILONE DERIVATIVE; EPOTHILONE F; TAXOL; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG SYNTHESIS; EPOXIDATION; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

ANTINEOPLASTIC AGENTS; EPOTHILONES; EPOXY COMPOUNDS; INDICATORS AND REAGENTS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLES;

EID: 0034604432     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20000804)6:15<2783::AID-CHEM2783>3.0.CO;2-B     Document Type: Article

References (116)

1. a) G. Höfle, N. Bedorf, K. Gerth, H. Reichenbach (GBF), DE-4138042, 1993 (Chem. Abstr. 1993, 120, 52841);
2. b) K. Gerth, N. Bedorf, G. Höfle, H. Irschik, H. Reichenbach, J. Antibiot. 1996, 49, 560-563;
3. c) G. Höfle, N. Bedorf, H. Steinmetz, D. Schomburg, K. Gerth, H. Reichenbach, Angew. Chem. 1996, 108, 1671-1673; Angew. Chem. Int. Ed. Engl. 1996, 35, 1567-1569.
4. c) G. Höfle, N. Bedorf, H. Steinmetz, D. Schomburg, K. Gerth, H. Reichenbach, Angew. Chem. 1996, 108, 1671-1673; Angew. Chem. Int. Ed. Engl. 1996, 35, 1567-1569.
5. K. C. Nicolaou, F. Roschangar, D. Vourloumis, Angew. Chem. 1998, 110, 2120-2153; Angew. Chem. Int. Ed. 1998, 37, 2014-2045.
6. K. C. Nicolaou, F. Roschangar, D. Vourloumis, Angew. Chem. 1998, 110, 2120-2153; Angew. Chem. Int. Ed. 1998, 37, 2014-2045.
7. Synthetic studies: a) K. C. Nicolaou, Y. He, D. Vourloumis, H. Vallberg, Z. Yang, Angew. Chem. 1996, 108, 2554-2556; Angew. Chem. Int. Ed. Engl. 1996, 35, 2399-2401;
8. Synthetic studies: a) K. C. Nicolaou, Y. He, D. Vourloumis, H. Vallberg, Z. Yang, Angew. Chem. 1996, 108, 2554-2556; Angew. Chem. Int. Ed. Engl. 1996, 35, 2399-2401;
9. b) D. Schinzer, A. Limberg, O. M. Böhm, Chem. Eur. J. 1996, 2, 1477-1482;
10. c) D. Meng, E. J. Sorensen, P. Bertinato, S. J. Danishefsky, J. Org. Chem. 1996, 61, 7998-7999;
11. d) P. Bertinato, E. J. Sorensen, D. Meng, S. J. Danishefsky, J. Org. Chem. 1996, 61, 8000-8001;
12. e) J. Mulzer, A. Mantoulidis, Tetrahedron Lett. 1996, 37, 9179-9182;
13. f) E. Claus, A. Pahl, P. G. Jones, H. M. Meyer, M. Kaiesse, Tetrahedron Lett. 1997, 38, 1359-1362;
14. g) T. Gabriel, L. Wessjohann, Tetrahedron Lett. 1997, 38, 1363-1366;
15. h) T. Gabriel, L. Wessjohann, Tetrahedron Lett. 1997, 38, 2061-2064;
16. i) J. D. Brabander, S. Rosset, G. Bernardinelli, Synlett 1997, 824-826;
17. j) J. Mulzer, A. Mantoulidus, E. Öhler, Tetrahedron Lett. 1997, 38, 7725-7728;
18. k) Z.-Y. Liu, C.-Z. Yu, J.-D. Yang, Synlett 1997, 1383-1384;
19. l) T. K. Chakraborty, S. Dutta, Tetrahedron Lett. 1998, 39, 101-104;
20. m) P. Bijoy, M. A. Avery, Tetrahedron Lett. 1998, 39, 209-212;
21. n) Z.-Y. Liu, C.-Z. Yu, R.-F. Wang, G. Li, Tetrahedron Lett. 1998, 39, 5261-5264;
22. o) K. Gerlach, M. Quitschalle, M. Kalesse, Synlett 1998, 1108-1110;
23. p) J. Mulzer, A. Mantoulidis, E. Öhler, Tetrahedron Lett. 1998, 39, 8633-8636;
24. q) K. Gerlach, M. Quitschalle, M. Kalesse, Tetrahedron Lett. 1999, 40, 3553-3556;
25. r) M. Quitschalle, M. Kalesse, Tetrahedron Lett. 1999, 40, 7765-7768.
26. Total and formal synthesis: a) A. Balog, D. Meng, T. Kamenecka, P. Bertinato, D.-S. Su, E. J. Sorensen, S. J. Danishefsky, Angew. Chem. 1996, 108, 2976-2978; Angew. Chem. Int. Ed. Engl. 1996, 35, 2801-2803;
27. Total and formal synthesis: a) A. Balog, D. Meng, T. Kamenecka, P. Bertinato, D.-S. Su, E. J. Sorensen, S. J. Danishefsky, Angew. Chem. 1996, 108, 2976-2978; Angew. Chem. Int. Ed. Engl. 1996, 35, 2801-2803;
28. b) Z. Yang, Y. He, D. Vourloumis, H. Vallberg, K. C. Nicolaou, Angew. Chem. 1997, 109, 170-172; Angew. Chem. Int. Ed. Engl. 1997, 36, 166-168;
29. b) Z. Yang, Y. He, D. Vourloumis, H. Vallberg, K. C. Nicolaou, Angew. Chem. 1997, 109, 170-172; Angew. Chem. Int. Ed. Engl. 1997, 36, 166-168;
30. c) K. C. Nicolaou, F. Sarabia, S. Ninkovic, Z. Yang, Angew. Chem. 1997, 109, 539-540; Angew. Chem. Int. Ed. Engl. 1997, 36, 525-526;
31. c) K. C. Nicolaou, F. Sarabia, S. Ninkovic, Z. Yang, Angew. Chem. 1997, 109, 539-540; Angew. Chem. Int. Ed. Engl. 1997, 36, 525-526;
32. d) D. Meng, D.-S. Su, A. Balog, P. Bertinato, E. J. Sorensen, S. J. Danishefsky, Y.-H. Zheng, T.-C. Chou, L. He, S. B. Horwitz, J. Am. Chem. Soc. 1997, 119, 2733-2734;
33. e) D. Schinzer, A. Limberg, A. Bauer, O. M. Böhm, M. Cordes, Angew. Chem. 1997, 109, 543-544; Angew. Chem. Int. Ed. Engl. 1997, 36, 523-524;
34. e) D. Schinzer, A. Limberg, A. Bauer, O. M. Böhm, M. Cordes, Angew. Chem. 1997, 109, 543-544; Angew. Chem. Int. Ed. Engl. 1997, 36, 523-524;
35. f) K. C. Nicolaou, Y. He, D. Vourloumis, H. Vallberg, F. Roschangar, F. Sarabia, S. Ninkovic, Z. Yang, J. I. Trujillo, J. Am. Chem. Soc. 1997, 119, 7960-7973;
36. g) K. C. Nicolaou, S. Ninkovic, F. Sarabia, D. Vourloumis, Y. He, H. Vallberg, M. R. V. Finlay, Z. Yang, J. Am. Chem. Soc. 1997, 119, 7974-7991;
37. h) D. Meng, P. Bertinato, A. Balog, D.-S. Su, T. Kamenecka, E. J. Sorensen, S. J. Danishefsky, J. Am. Chem. Soc. 1997, 119, 10073-10092;
38. i) K. C. Nicolaou, N. Winssinger, J. A. Pastor, S. Ninkovic, F. Sarabia, Y. He, D. Vourloumis, Z. Yang, T. Li, P. Giannakakou, E. Hamel, Nature 1997, 387, 268-272;
39. j) D.-S. Su, D. Meng, P. Bertinato, A. Balog, E. J. Sorensen, S. J. Danishefsky, Y.-H. Zheng, T.-C. Chou, L. He, S. B. Horwitz, Angew. Chem. 1997, 109, 775-777; Angew. Chem. Im. Ed. Engl. 1997, 36, 757-759;
40. j) D.-S. Su, D. Meng, P. Bertinato, A. Balog, E. J. Sorensen, S. J. Danishefsky, Y.-H. Zheng, T.-C. Chou, L. He, S. B. Horwitz, Angew. Chem. 1997, 109, 775-777; Angew. Chem. Im. Ed. Engl. 1997, 36, 757-759;
41. k) D. Schinzer, A. Bauer, J. Scheiber, Synlett 1998, 861-864;
42. l) S. A. May, P. Grieco, Chem. Commun. 1998, 1597-1598;
43. m) A. Balog, C. Harris, K. Savin, X.-G. Zhang, T. C. Chou, S. J. Danishefsky, Angew. Chem. 1998, 110, 2821-2824; Angew. Chem. Int. Ed. 1998, 37, 2675-2678;
44. m) A. Balog, C. Harris, K. Savin, X.-G. Zhang, T. C. Chou, S. J. Danishefsky, Angew. Chem. 1998, 110, 2821-2824; Angew. Chem. Int. Ed. 1998, 37, 2675-2678;
45. n) R. E. Taylor, G. M. Galvin, K. A. Hilfiker, Y. Chen, J. Org. Chem. 1999, 64, 7224-7227;
46. o) S. C. Sinha, C. F. Barbas III, R. A. Lerner, Proc. Natl. Acad. Sci. USA 1998, 95, 14603-14608;
47. p) J. D. White, R. G. Carter, K. F. Sundermann, J. Org. Chem. 1999, 64, 684-685;
48. q) C. R. Harris, S. D. Kuduk, A. Balog, K. Savin, P. W. Glunz, S. J. Danishefsky, J. Am. Chem. Soc. 1999, 121, 7050-7062;
49. r) M. Kalesse, M. Quitschalle, E. Claus, K. Gerlach, A. Pahl, H. H. Meyer, Eur. J. Org. Chem. 1999, 2817-2823;
50. s) D. Schinzer, A. Bauer, O. M. Böhm, A. Limberg, M. Cordes, Chem. Eur. J. 1999, 5, 2483-2491;
51. t) D. Schinzer, A. Bauer, J. Schieber, Chem. Eur. J. 1999, 5, 2492-2500;
52. u) J. D. White, K. F. Sundermann, R. G. Carter, Org. Lett. 1999, 1, 1431-1434;
53. v) S. C. Sinha, J. S. Sun, G. Miller, C. F. Barbas III, R. A. Lerner, Org. Lett. 1999, 1, 1623-1626;
54. w) D. Sawada, M. Shibasaki, Angew. Chem. 2000, 112, 215-219; Angew. Chem. Int. Ed. 2000, 39, 209-213;
55. w) D. Sawada, M. Shibasaki, Angew. Chem. 2000, 112, 215-219; Angew. Chem. Int. Ed. 2000, 39, 209-213;
56. x) H. J. Martin, M. Drescher, J. Mulzer, Angew. Chem. 2000, 112, 591-593; Angew. Chem. Int. Ed. 2000, 39, 581-583.
57. x) H. J. Martin, M. Drescher, J. Mulzer, Angew. Chem. 2000, 112, 591-593; Angew. Chem. Int. Ed. 2000, 39, 581-583.
58. a) A. Balog, P. Bertinato, D.-S. Su, D. Meng, E. J. Sorensen, S. J. Danishefsky, Y.-H. Zheng, T.-C. Chou, L. He, S. B. Horwitz, Tetrahedron Lett. 1997, 38, 4529-4532;
59. b) K. C. Nicolaou, F. Sarabia, M. R. V. Finlay, S. Ninkovic, N. P. King, D. Vourloumis, Y. He, Chem. Eur. J. 1997, 3, 1971-1986;
60. c) K. C. Nicolaou, H. Vallberg, N. P. King, F. Roschangar, Y. He, D. Vourloumis, C. G. Nicolaou, Chem. Eur. J. 1997, 3, 1957-1970;
61. d) D.-S. Su, A. Balog, D. Meng, P. Bertinato, S. J. Danishefsky, Y.-H. Zheng, T.-C. Chou, L. He, S. B. Horwitz, Angew. Chem. 1997, 109, 2178-2181; Angew. Chem. Int. Ed. Engl. 1997, 36, 2093-2096;
62. d) D.-S. Su, A. Balog, D. Meng, P. Bertinato, S. J. Danishefsky, Y.-H. Zheng, T.-C. Chou, L. He, S. B. Horwitz, Angew. Chem. 1997, 109, 2178-2181; Angew. Chem. Int. Ed. Engl. 1997, 36, 2093-2096;
63. e) K. C. Nicolaou, D. Vourloumis, T. Li, J. Pastor, N. Winssinger, Y. He, S. Ninkovic, F. Sarabia, H. Vallberg, F. Roschangar, N. P. King, M. R. V. Finlay, P. Giannakakou, P. Verdier-Pinard, E. Hamel, Angew. Chem. 1997, 108, 2181-2187; Angew. Chem. Int. Ed. Engl. 1997, 36, 2097-2103;
64. e) K. C. Nicolaou, D. Vourloumis, T. Li, J. Pastor, N. Winssinger, Y. He, S. Ninkovic, F. Sarabia, H. Vallberg, F. Roschangar, N. P. King, M. R. V. Finlay, P. Giannakakou, P. Verdier-Pinard, E. Hamel, Angew. Chem. 1997, 108, 2181-2187; Angew. Chem. Int. Ed. Engl. 1997, 36, 2097-2103;
65. f) K. C. Nicolaou, S. Ninkovic, M. R. V. Finlay, F. Sarabia, Chem. Commun. 1997, 2343-2344;
66. g) K. C. Nicolaou, F. Sarabia, S. Ninkovic, M. R. V. Finlay, C. N. C. Boddy, Angew. Chem. 1998, 110, 85-89; Angew. Chem. Int. Ed. 1998, 37, 81-84;
67. g) K. C. Nicolaou, F. Sarabia, S. Ninkovic, M. R. V. Finlay, C. N. C. Boddy, Angew. Chem. 1998, 110, 85-89; Angew. Chem. Int. Ed. 1998, 37, 81-84;
68. h) K. C. Nicolaou, Y. He, F. Roschangar, N. P. King, D. Vourloumis, T. Li, Angew. Chem. 1998, 110, 89-92; Angew. Chem. Int. Ed. 1998, 37, 84-87;
69. h) K. C. Nicolaou, Y. He, F. Roschangar, N. P. King, D. Vourloumis, T. Li, Angew. Chem. 1998, 110, 89-92; Angew. Chem. Int. Ed. 1998, 37, 84-87;
70. i) K. C. Nicolaou, M. R. V. Finlay, S. Ninkovic, F. Sarabia, Tetrahedron 1998, 54, 7127-7166;
71. j) K. C. Nicolaou, M. R. V. Finlay, S. Ninkovic, N. P. King, Y. He, T. Li, F. Sarabia, D. Vourloumis, Chem. Biol. 1998, 5, 365-372;
72. k) K. C. Nicolaou, N. P. King, M. R. V. Finlay, Y. He, F. Roschangar, D. Vourloumis, H. Vallberg, F. Sarabia, S. Ninkovic, D. Hepworth, Bioorg. Med. Chem. 1999, 7, 665-697;
73. l) T.-C. Chou, X.-G. Zhang, A. Balog, D.-S. Su, D. Meng, K. Savin, J. R. Bertino, S. J. Danishefsky, Proc. Natl. Acad. Sci. USA 1998, 95, 9642-9647;
74. m) J. D. Winkler, J. M. Holland, J. Kasparec, P. H. Axelsen, Tetrahedron 1999, 55, 8199-8214.
75. a) H. Reichenbach, G. Höfle, K. Gerth, H. Steinmettz, (GBF) WO-A 9822461, 1998 (Chem. Abstr. 1998, 129, 5346);
76. b) G. Höfle in GBF Annual Report (Ed.: J.-H. Walsdorff), GBF, Braunschweig, 1997, pp. 91-92.
77. a) M. Sefkow, M. Kiffe, D. Schummer, G. Höfle, Bioorg. Med. Chem. Lett. 1998, 8, 3025-3030;
78. b) M. Sefkow, M. Kiffe, G. Höfle, Bioorg. Med. Chem. Lett. 1998, 8, 3031-3036;
79. c) M. Sefkow, G. Höfle, Heterocycles 1998, 48, 2485-2488;
80. d) G. Höfle, N. Glaser, M. Kiffe, H.-J. Hecht, F. Sasse, H. Reichenbach, Angew. Chem. 1999, 111, 2090-2093; Angew. Chem. Int. Ed. 1999, 38, 1971-1974.
81. d) G. Höfle, N. Glaser, M. Kiffe, H.-J. Hecht, F. Sasse, H. Reichenbach, Angew. Chem. 1999, 111, 2090-2093; Angew. Chem. Int. Ed. 1999, 38, 1971-1974.
82. a) D. M. Bollag, P. A. McQueney, J. Zhu, O. Hensens, L. Koupal, J. Liesch, M. Goetz, E. Lazarides, C. M. Woods, Cancer Res. 1995, 55, 2325-2333;
83. b) R. J. Kowalski, P. Giannakakou, E. Hamel, J. Biol. Chem. 1997, 272, 2534-2541.
84. S. B. Horwitz, J. Fant, P. B. Schiff, Nature 1979, 277, 665-667.
85. K. C. Nicolaou, D. Hepworth, M. R. V. Finlay, N. P. King, B. Werschkun, A. Bigot, Chem. Commun. 1999, 519-520.
86. For a recent example see: V. H. Rawal, R. C. Newton, V. Krishnamurthy, J. Org. Chem. 1990, 55, 5181-5183, and references therein.
87. R. O. Hutchins, D. Kandasamy, C. A. Maryanoff, D. Masilamani, B. E. Maryanoff, J. Org. Chem. 1977, 42, 82-91.
88. M. Tamura, J. Kochi, Synthesis 1971, 303-305.
89. Y. Morimoto, H. Shirahama, Tetrahedron 1996, 52, 10631-10652.
90. The racemate was prepared by addition of allylmagnesium bromide to aldehyde 29 (THF, -78°C). The chiral HPLC was conducted using Chiralcel OD-H column eluting with 10% 2-propanol in hexanes.
91. R. D. Clark, L. G. Kozar, C. H. Heathcock, Synthesis 1975, 635-636.
92. C. H. Heathcock in Comprehensive Organic Synthesis, Vol. 2 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, pp. 181-238.
93. a) J. R. Parikh, W. V. E. Doering, J. Am. Chem. Soc. 1967, 89, 5505-5507;
94. b) S. V. Ley, J. Norman, W. P. Griffith, S. P. Marsden, Synthesis 1994, 639-666;
95. c) T. T. Tidwell in Encyclopedia of Reagents for Organic Synthesis (Ed.: L. A. Paquette), Wiley, New York, 1995, pp. 2149-2152.
96. For a recent example of a similar kinetic ketone lithium enolate aldol reaction see: I. Paterson, D. J. Wallace, R. M. Oballa, Tetrahedron Lett. 1998, 39, 8545-8548.
97. a) J. Inanaga, K. Hirata, H. Saeki, T. Katsuki, M. Yamaguchi, Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993;
98. b) J. Mulzer, P. A. Mareski, J. Bushmann, P. Luger, Synthesis 1992, 215-228;
99. c) K. C. Nicolaou, A. P. Patron, K. Ajito, P. K. Richter, H. Khatuya, P. Bertinato, R. A. Miller, M. J. Tomaszewski, Chem. Eur. J. 1996, 2, 847-868.
100. T. Katsuki, K. B. Sharpless, J. Am. Chem. Soc. 1980, 102, 5976-5978.
101. a) J. K. Stille, Angew. Chem. 1986, 98, 504-522; Angew. Chem. Int. Ed. Engl. 1986, 25, 508-524.
102. a) J. K. Stille, Angew. Chem. 1986, 98, 504-522; Angew. Chem. Int. Ed. Engl. 1986, 25, 508-524.
103. For a recent review see: b) V. Farina, V. Krishnamurthy, J. W. Scott, Org. React. 1997, 50, 1-652.
104. V. Farina, G. P. Roth, Adv. Metal. Org. Chem. 1996, 5, 1-53.
105. a) L. S. Liebeskind, R. W. Fengl, J. Org. Chem. 1990, 55, 5359-5364;
106. b) V. Farina, S. Kapadia, B. Krishnan, C. Wang, L. S. Liebeskind, J. Org. Chem. 1994, 59, 5905-5911.
107. V. Farina, B. Krishnan, J. Am. Chem. Soc. 1991, 113, 9585-9595.
108. L. Hegedus, B. Lipshutz, H. Nozaki, M. Reetz, P. Rittmeyer, K. Smith, F. Totter, H. Yamamoto in Organometallics in Synthesis (Ed.: M. Schlosser), Wiley, Chinchester, 1994, p. 286.
109. K. C. Nicolaou, et al., unpublished results.
110. a) K. R. Wursthorn, H. G. Kuivila, J. Organomet. Chem. 1977, 140, 29-39;
111. b) W. Kaim, H. Tesmann, H. Bock, Chem. Ber. 1980, 113, 3221-3234;
112. c) C. Bolm, M. Ewald, E. Felder, G. Schlingloff, Chem. Ber. 1992, 125, 1169-1190;
113. d) Z. Bao, W. K. Chan, L. Yu, J. Am. Chem. Soc. 1995, 117, 12426-12435;
114. e) G. S. Hanan, U. S. Schubert, D. Volkmer, E. Rivière, J.-M. Lehn, N. Kyritsakas, J. Fischer, Can. J. Chem. 1997, 75, 169-182;
115. f) E. M. Driggers, H. S. Cho, C. W. Liu, C. P. Katzka, A. C. Braisted, H. D. Ulrich, D. Wemmer, P. G. Schultz, J. Am. Chem. Soc. 1998, 120, 1945-1952.
116. K. C. Nicolaou, R. Scarpelli, B. Bollbuck, B. Werschkun, M. M. A. Pereira, M. Wartmann, K.-H. Altmann, D. Zaharevitz, R. Gussio, P. Giannakakou, Chem. Biol., in press.