Total Synthesis of the Polyene-Polyol Macrolide RK-397, Featuring Cross-Couplings of Alkynylepoxide Modules

Journal of the American Chemical Society

Volumn 126, Issue 8, 2004, Pages 2495-2500

  Burova, Svetlana A ^a   McDonald, Frank E ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CARBON; CHEMICAL BONDS; ISOMERS; KETONES; ORGANIC POLYMERS; OXIDATION; STEREOCHEMISTRY;

HYDROSILYLATION; NATURAL PRODUCTS;

SYNTHESIS (CHEMICAL);

ALKYNYL GROUP; EPOXIDE; HYDROXYL GROUP; KETONE; MACROLIDE; NATURAL PRODUCT; POLYENE ANTIBIOTIC AGENT; POLYOL; RK 397; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CROSS COUPLING REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROSILYLATION; OXIDATION; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; STEREOISOMERISM;

ALKYNES; EPOXY COMPOUNDS; MACROLIDES;

EID: 1542306890     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja039618+     Document Type: Article

References (84)

1. Maehr, H.; Yang, R.; Hong, L. N.; Liu, C. M.; Hatada, M. H.; Todaro, L. J. J. Org. Chem. 1989, 54, 3816.
2. (b) Wasserman, H. H.; Van Verth, J. E.; McCaustland, D. J.; Borowitz, I. J.; Kamber, B. J. Am. Chem. Soc. 1967, 89, 1535.
3. (c) Schreiber, S. L.; Goulet, M. T. J. Am. Chem. Soc. 1987, 109, 8120.
4. (d) Lancelin, J. M.; Beau, J. M. Tetrahedron Lett. 1989, 30, 4521.
5. Kobinata, K.; Koshino, H.; Kudo, T.; Isono, K.; Osada, H. J. Antibiot. 1993, 46, 1616.
6. (b) Koshino, H.; Kobinata, K.; Isono, K.; Osada, H. J. Antibiot. 1993, 46, 1619.
7. (c) Suenaga, T.; Nakamura, H.; Koshino, H.; Kobinata, K.; Osada, H.; Nakata, T. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1997, 39, 607 (Chem. Abstr. 1997, 131, 129786).
8. (c) Suenaga, T.; Nakamura, H.; Koshino, H.; Kobinata, K.; Osada, H.; Nakata, T. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1997, 39, 607 (Chem. Abstr. 1997, 131, 129786).
9. Drug Facts and Comparisons; Wolters Kluwer: St Louis, 1996; pp 2174, 2180.
10. (a) Enzymatic Reaction Mechanisms, Walsh, C., Ed.; W. H. Freeman: San Francisco, 1979; pp 909-916.
11. (b) Staunton, J. Angew. Chem., Int. Ed. Engl. 1991, 30, 1302.
12. (c) Cortes, J.; Haydock, S. F.; Roberts, G. A.; Bevitt, D. J.; Leadlay, P. F. Nature 1990, 348, 176.
13. (d) Donadio, S.; Staver, M. J.; McAlpine, J. B.; Swanson, S. J.; Katz, L. Science 1999, 252, 675.
14. (e) Tsoi, C. J.; Khosla, C. Chem. Biol. 1995, 2, 355.
15. (f) Rohr, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 881.
16. (g) Bailey, J. E. Nat. Biotechnol. 1999, 17, 616.
17. (h) Cane, D. E.; Walsh, C. T.; Khosla, C. Science 1998, 282, 63.
18. (i) Carreras, C. W.; Santi, D. V. Curr. Opin. Biotechnol. 1998, 9, 403.
19. Poss, C. S.; Rychnovsky, S. D.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 3360.
20. (b) Roush, W. R.; Palkowitz, A. D.; Ando, K. J. Am. Chem. Soc. 1990, 112, 6348.
21. (c) Andersen, M. W.; Hildebrandt, B.; Dahmann, G.; Hoffmann, R. W. Chem. Ber. 1991, 124, 2127.
22. Carreira, E. M.; Singer, R. A.; Lee, W. J. Am. Chem. Soc. 1994, 116, 8837.
23. See also (b) Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127.
24. (c) Cowden, C. J.; Paterson, I. Org. React. 1997, 51, 1.
25. (d) Abiko, A.; Liu, J.-F.; Masamune, S. J. Am. Chem. Soc. 1997, 119, 2586.
26. (e) Lalic, G.; Aloise, A. D.; Shair, M. D. J. Am. Chem. Soc. 2003, 125, 2852.
27. (f) Huckin, S. N.; Weiler, L. J. Am. Chem. Soc. 1974, 96, 1082.
28. (g) Huckin, S. N.; Weiler, L. Can. J. Chem. 1974, 52, 1343.
29. (h) Harris, T. M.; Harris, C. M.; Kuzma, P. C.; Lee, J. Y. C.; Mahalingam, S.; Gilbreath, S. G. J. Am. Chem. Soc. 1988, 110, 6186.
30. (i) Yamaguchi, M.; Hasebe, K.; Higashi, H.; Uchida, M.; Irie, A.; Minami, T. J. Org. Chem. 1990, 55, 1611.
31. (j) Singer, R. A.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 12360.
32. (k) Evans, D. A.; Gauchet-Prunet J. A.; Carreira, E. M.; Charette, A. B. J. Org. Chem. 1991, 56, 741.
33. Rychnovsky, S. D.; Zeller, S.; Skalitzky, D. J.; Griesgraber, G. J. Org. Chem. 1990, 55, 5550.
34. (b) Rychnovsky, S. D.; Rogers, B. N.; Richardson, T. I. Acc. Chem. Res. 1998, 31, 9, and refs 8h,j-l.
35. For other synthetic work in the area of polyol-polyene macrolides, see: Amphotericin B: (a) Nicolaou, K. C.; Daines, R. A.; Ogawa, Y.; Chakraborty, T. K. J. Am. Chem. Soc. 1988, 110, 4696.
36. (b) Nicolaou, K. C.; Daines, R. A.; Uenishi, J.; Li, W. S.; Papahatjis, D. P.; Chakraborty, T. K. J. Am. Chem. Soc. 1988, 110, 4672.
37. Mycoticin A: (c) see ref 5a.
38. (d) Dreher, S. D.; Leighton, J. L. J. Am. Chem. Soc. 2001, 123, 341.
39. Roxaticin: (e) Mori, Y.; Asai, M.; Kawade, J.-I.; Furukawa, H. Tetrahedron 1995, 51, 5315.
40. (f) Mori, Y.; Asai, M.; Okumura, A.; Furukawa, H. Tetrahedron 1995, 51, 5299.
41. (g) Mori, Y.; Asai, M.; Kawade, J.-I.; Okumura, A.; Furukawa, H. Tetrahedron Lett. 1994, 35, 6503.
42. (h) Rychnovsky, S. D.; Hoye, R. C. J. Am. Chem. Soc. 1994, 116, 1753.
43. (i) Evans, D. A.; Connell, B. T. J. Am. Chem. Soc. 2003, 125, 10899.
44. Roflamycoin: (j) Rychnovsky, S. D.; Khire, U. R.; Yang, G. J. Am. Chem. Soc. 1997, 119, 2058.
45. Dermostatin A: (k) Sinz, C. J.; Rychnovsky, S. D. Tetrahedron 2002, 58, 6561.
46. (l) Sinz, C. J.; Rychnovsky, S. D. Angew. Chem., Int. Ed. 2001, 40, 3224.
47. (m) Filipin III: Richardson, T. I.; Rychnovsky, S. D. J. Am. Chem. Soc. 1997, 119, 12360.
48. Syn-reduction of β-hydroxyketones: (a) Nakata, T.; Takao, S.; Fukui, M.; Oishi, T. Tetrahedron Lett. 1983, 24, 3873.
49. (b) Chen, K.-M.; Hardtmann, G.; Prasad, K.; Repic, O.; Shapiro, M. J. Tetrahedron Lett. 1987, 28, 155.
50. Anti-reduction of β-hydroxyketones: (c) Saksena, A. K.; Mangiaracina, P. Tetrahedron Lett. 1983, 24, 273.
51. (d) Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447.
52. (e) Keck, G. E.; Wager, C. A.; Sell, T.; Wager, T. T. J. Org. Chem. 1999, 64, 2172.
53. Burova, S. A.; McDonald, F. E. J. Am. Chem. Soc. 2002, 124, 8188.
54. For a different approach to the RK-397 polyol, see: Schneider, C.; Tolksdorf, F.; Rehfeuter, M. Synlett 2002, 12, 2098.
55. Nicolaou, K. C.; Seitz, S. P.; Pavia M. R. J. Am. Chem. Soc. 1982, 104, 2030.
56. (b) Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, A. P.; Masamune, S.; Roush, W. R.; Sakai, T. Tetrahedron Lett. 1984, 25, 2183.
57. Brown, H. C.; Bhat, K. S. J. Am. Chem. Soc. 1986, 108, 5919.
58. (b) For 15, see ref 8d.
59. (c) For compound ent-15, see: Ghosh, A. K.; Liu, W. J. Org. Chem. 1997, 62, 7908.
60. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953.
61. Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168.
62. (b) Gessler, S.; Randl, S.; Blechert, S. Tetrahedron Lett. 2000, 41, 9973.
63. Paterson, I.; Goodman, J. M. Tetrahedron Lett. 1989, 30, 997.
64. (b) Paterson, I.; Goodman, J. M.; Lister, M. A.; Schumann, R. C.; McClure, C. K.; Norcross, R. D. Tetrahedron 1990, 46, 4663.
65. Paterson, I.; Perkins, M. V. Tetrahedron Lett. 1992, 33, 801.
66. (b) Paterson, I.; Perkins, M. V. Tetrahedron 1996, 52, 1811.
67. Although a similar reaction sequence could be accomplished from 19 to give the silyl ether analogue of 23, the mixture of diastereomers could not be efficiently separated.
68. Relative and absolute configuration of 23 was confirmed by X-ray diffraction analysis of the secondary alcohol resulting from DDQ oxidative removal of the p-methoxybenzyl ether protective group. Please see Supporting Information for details.
69. Annis, D. A.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 4147.
70. (b) Furrow, M. E.; Schaus, S. E.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 6776.
71. (c) Schaus, S. E.; Brandes, B. D.; Larrow, J. F.; Tokunaga, M.; Hansen, K. B.; Gould, A. E.; Furrow, M. E.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 1307.
72. Schuda, A.; Mazzocchi, P. H.; Fritz, G.; Morgan, T. Synthesis 1986, 309.
73. (b) For a different enantioselective synthesis of 34, see: Zemribo, R.; Mead, K. T. Tetrahedron Lett. 1998, 39, 3895.
74. Yamaguchi, M.; Hirao, I. Tetrahedron Lett. 1983, 24, 391.
75. Marshall, J. A.; Yanik, M. M. J. Org. Chem. 1999, 64, 3798.
76. Iodocyclization of the tert-butyl carbonate derivative of the alcohol of 38 was successful. However radical deiodination resulted in a product attributed to radical cyclization onto the C28-C29 alkene. Please see Supporting Information for more discussion.
77. Tamao, K.; Maeda, K.; Tanaka, T.; Ito, Y. Tetrahedron Lett. 1988, 29, 6955.
78. (b) Marshall, J. A.; Yanik, M. M. Org. Lett. 2000, 2, 2173.
79. Denmark, S. E.; Wang, Z. Org. Lett. 2001, 3, 1073.
80. 6) even after extended reaction time. Cyclic siloxane 41 suffered significant decomposition upon prolonged exposure to silica gel; therefore, it was taken to the next step without purification.
81. 2.
82. (b) Review: Wipf, P.; Jahn, H. Tetrahedron 1996, 52, 12853.
83. 2, -78 °C (75% yield).
84. 1H NMR spectra and ultraviolet spectra of natural RK-397 (4) and its tetraacetonide derivative 52 were generously provided by Dr. Tadashi Nakata and Dr. Hiroyuki Koshino from The Institute of Physical and Chemical Research (RIKEN), Japan.