Convergent total synthesis of gymnocin-A and evaluation of synthetic analogues

Journal of the American Chemical Society

Volumn 127, Issue 12, 2005, Pages 4326-4335

  Tsukano, Chihiro ^a   Ebine, Makoto ^a   Sasaki, Makoto ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

STEREOCHEMISTRY; SYNTHESIS (CHEMICAL); TOXIC MATERIALS;

CYTOTOXIC POLYCYCLIC ETHERS; GYMNOCIN-A; RING FRAGMENTS; STRUCTURAL ANALOGUES;

POLYETHERS;

2 METHYL 2 BUTENAL; ALDEHYDE DERIVATIVE; CYTOTOXIC AGENT; GYMNOCIN A; HYDROXYL GROUP; POLYETHER; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; CROSS COUPLING REACTION; CYCLIZATION; DINOFLAGELLATE; DRUG CYTOTOXICITY; HYDROBORATION; KARENIA MIKIMOTOI; LEUKEMIA P 388; MOUSE; NONHUMAN; NUCLEAR OVERHAUSER EFFECT; RED TIDE; RING CLOSING METATHESIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; SUZUKI MIYAURA REACTION; SYNTHESIS;

ANIMALS; DINOFLAGELLIDA; ETHERS, CYCLIC; MODELS, MOLECULAR;

EID: 16244420716     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja042686r     Document Type: Article

References (93)

1. Lin, Y.-Y.; Risk, M.; Ray, S. M.; Van Engen, D.; Clardy, J.; Golik, J.; James, J. C.; Nakanishi, K. J. Am. Chem. Soc. 1981, 103, 6773.
2. For reviews on marine polycyclic ethers, see: (a) Yasumoto, T.; Murata, M. Chem. Rev. 1993, 93, 1897.
3. (b) Murata, M.; Yasumoto, T. Nat. Prod. Rep. 2000, 293.
4. (c) Yasumoto, T. Chem. Rec. 2001, 1, 228.
5. For reviews on polycyclic ether synthesis, see: (a) Alvarez, E.; Candenas, M.-L.; Pérez, R.; Ravelo, J. L.; Martín, J. D. Chem. Rev. 1995, 95, 1953.
6. (b) Mori, Y. Chem.-Eur. J. 1997, 3, 849.
7. (c) Marmsäter, F. P.; West, F. G. Chem.-Eur. J. 2002, 8, 4346.
8. (d) Evans, P. A.; Delouvrie, B. Curr. Opin. Drug Discovery Dev. 2002, 5, 986.
9. (e) Inoue, M. Org. Biomol. Chem. 2004, 2, 1811.
10. (a) Nicolaou, K. C.; Reddy, K. R.; Skokotas, G.; Sato, F.; Xiao, X.-Y.; Hwang, C.-K. J. Am. Chem. Soc. 1993, 115, 3558.
11. (b) Kadota, I.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6597.
12. (c) Morimoto, M.; Matsukura, H.; Nakata, T. Tetrahedron Lett. 1996, 37, 6365.
13. (d) Mori, Y.; Yaegassi, K.; Furukawa, H. J. Org. Chem. 1998, 63, 6200.
14. (e) Rainier, J. D.; Allwein, S. P.; Cox, J. M. J. Org. Chem. 2001, 66, 1380.
15. (f) Zakarian, A.; Batch, A.; Holton, R. A. J. Am. Chem. Soc. 2003, 125, 7822.
16. (g) Fujiwara, K.; Sato, D.; Watanabe, M.; Morishita, H.; Murai, A.; Kawai, H.; Suzuki, T. Tetrahedron Lett. 2004, 45, 5243.
17. (a) Nicolaou, K. C.; Theodorakis, E. A.; Rutjes, F. P. J. T.; Tiebes, J.; Sato, M.; Untersteller, E.; Xiao X.-Y. J. Am. Chem. Soc. 1995, 117, 1171.
18. (b) Nicolaou, K. C.; Rutjes, F. P. J. T.; Theodorakis, E.; Tiebes, J.; Sato, M.; Untersteller, E. J. Am. Chem. Soc. 1995, 117, 1173.
19. (c) Nicolaou, K. C.; Hwang, C.-K.; Duggan, M. E.; Nugiel, D. A.; Abe, Y.; Bal Reddy, K.; DeFrees, S. A.; Reddy, D. R.; Awartani, R. A.; Conley, S. R.; Rutjes, F. P. J. T.; Theodorakis, E. A. J. Am. Chem. Soc. 1995, 117, 10227.
20. (d) Nicolaou, K. C.; Theodorakis, E. A.; Rutjes, F. P. J. T.; Sato, M.; Tiebes, J.; Xiao, X.-Y.; Hwang, C.-K.; Duggan, M. E.; Yang, Z.; Couladouros, E. A.; Sato, F.; Shin, J.; He, H.-M.; Bleckman, T. J. Am. Chem. Soc. 1995, 117, 10239.
21. (e) Nicolaou, K. C.; Rutjes, F. P. J. T.; Theodorakis, E. A.; Tiebes, J.; Sato, M.; Untersteller, E. J. Am. Chem. Soc. 1995, 117, 10252.
22. Matsuo, G.; Kawamura, K.; Hori, N.; Matsukura, H.; Nakata, T. J. Am. Chem. Soc. 2004, 126, 14374.
23. (a) Nicolaou, K. C.; Yang, Z.; Shi, G.-Q.; Gunzner, J. L.; Agrios, K. A.; Gärtner, P. Nature 1998, 392, 264.
24. (b) Nicolaou, K. C.; Bunnage, M. E.; McGarry, D. G.; Shi, S.; Somers, P. K.; Wallace, P. A.; Chu, X.-J.; Agrios, K. A.; Gunzner, J. L.; Yang, Z. Chem.-Eur. J. 1999, 5, 599.
25. (c) Nicolaou, K. C.; Wallace, P. A.; Shi, S.; Ouellette, M. A.; Bunnage, M. E.; Gunzner, J. L.; Agrios, K. A.; Shi, G.-Q.; Gärtner, P.; Yang, Z. Chem.-Eur. J. 1999, 5, 618.
26. (d) Nicolaou, K. C.; Shi, G.-Q.; Gunzner, J. L.; Gärtner, P.; Wallace, P. A.; Ouellete, M. A.; Shi, S.; Bunnage, M. E.; Agrios, K. A.; Veale, C. A.; Hwang, C.-K.; Hutchinson, J.; Prasad, C. V. C.; Ogilvie, W. W.; Yang, Z. Chem.-Eur. J. 1999, 5, 628.
27. (e) Nicolaou, K. C.; Gunzner, J. L.; Shi, G.-Q.; Agrios, K. A.; Gärtner, P.; Yang, Z. Chem.-Eur. J. 1999, 5, 646.
28. (a) Hirama, M.; Oishi, T.; Uehara, H.; Inoue, M.; Maruyama, M.; Oguri, H.; Satake, M. Science 2001, 294, 1904.
29. (b) Inoue, M.; Uehara, H.; Maruyama, M.; Hirama, M. Org. Lett. 2002, 4, 4551.
30. (c) Inoue, M.; Hirama, M. Synlett 2004, 4, 577.
31. (d) Inoue, M.; Miyazaki, K.; Uehara, H.; Maruyama, M.; Hirama, M. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 12013.
32. (e) Inoue, M.; Hirama, M. Acc. Chem. Res. 2004, 37, 961.
33. (a) Fuwa, H.; Sasaki, M.; Satake, M.; Tachibana, K. Org. Lett. 2002, 4, 2981.
34. (b) Fuwa, H.; Kainuma, N.; Tachibana, K.; Sasaki, M. J. Am. Chem. Soc. 2002, 124, 14983.
35. (a) Kadota, I.; Takamura, H.; Sato, K.; Ohno, A.; Matsuda, K.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 46.
36. (b) Kadota, I.; Takamura, H.; Sato, K.; Ohno, A.; Matsuda, K.; Satake, M.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 11893.
37. (c) Johnson, H. W. B.; Majumder, U.; Rainier, J. D. J. Am. Chem. Soc. 2005, 127, 848.
38. Satake, M.; Shoji, M.; Oshima, Y.; Naoki, H.; Fujita, T.; Yasumoto, T. Tetrahedron Lett. 2002, 43, 5829.
39. Private communication with Professor M. Satake of Tohoku University in 2001.
40. For reviews on the Suzuki-Miyaura cross-coupling reaction, see: (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
41. (b) Suzuki, A. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998; p 49.
42. (c) Suzuki, A. J. Organomet. Chem. 1999, 576, 147.
43. (d) Chemler, S. R.; Trauner, D.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2001, 40, 4544.
44. (e) Miyaura, N. In Topics in Current Chemistry; Springer-Verlag: Heidelberg, Germany, 2002; Vol. 219, p 11.
45. (f) Suzuki, A.; Brown, H. C. In Organic Syntheses Via Boranes; Aldrich Chem. Co.: Milwaukee, WI, 2003; Vol. 3.
46. (a) Sasaki, M.; Fuwa, H.; Inoue, M.; Tachibana, K. Tetrahedron Lett. 1998, 39, 9027.
47. (b) Sasaki, M.; Fuwa, H.; Ishikawa, M.; Tachibana, K. Org. Lett. 1999, 1, 1075.
48. (c) Fuwa, H.; Sasaki, M.; Tachibana, K. Tetrahedron 2001, 57, 3019.
49. (d) Fuwa, H.; Sasaki, M.; Tachibana, K. Org. Lett. 2001, 3, 3549.
50. (e) Takakura, H.; Noguchi, K.; Sasaki, M.; Tachibana, K. Angew. Chem., Int. Ed. 2001, 40, 1090.
51. (f) Sasaki, M.; Ishikawa, M.; Fuwa, H.; Tachibana, K. Tetrahedron 2002, 58, 1889.
52. (g) Takakura, H.; Sasaki, M.; Honda, S.; Tachibana, K. Org. Lett. 2002, 4, 2771.
53. (h) Fuwa, H.; Fujikawa, S.; Tachibana, K.; Takakura, H.; Sasaki, M. Tetrahedron Lett. 2004, 45, 4795.
54. Initial communications of this work: (a) Sasaki, M.; Tsukano, C.; Tachibana, K. Org. Lett. 2002, 4, 1747.
55. (b) Sasaki, M.; Tsukano, C.; Tachibana, K. Tetrahedron Lett. 2003, 44, 4351.
56. (c) Tsukano, C.; Sasaki, M. J. Am. Chem. Soc. 2003, 125, 14294.
57. Details of the synthesis of compounds 10, 25, 39, and 68 are included in Supporting Information.
58. The corresponding diastereomeric alcohol was obtained in ca. 10% yield.
59. Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639.
60. Nicolaou, K. C.; Prasad, C. V. C.; Hwang, C.-K.; Duggan, M. E.; Veale, C. A. J. Am. Chem. Soc. 1989, 111, 5321. See also refs 9b and 14d,e,g.
61. (a) Freeman, P. K.; Hutchinson, L. L. J. Org. Chem. 1980, 45, 1924.
62. (b) Ireland, R. E.; Smith, M. G. J. Am. Chem. Soc. 1988, 110, 854.
63. Ito, Y.; Hirao, T.; Saegusa, T. J. Org. Chem. 1978, 43, 1011.
64. Luche, J. L. J. Am. Chem. Soc. 1978, 100, 2226.
65. For a review, see: Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307.
66. Miyashita, M.; Suzuki, T.; Hoshino, M.; Yoshikoshi, A. Tetrahedron 1997, 53, 12469.
67. For recent examples for β-alkoxyacrylate radical cyclization, see: (a) Kang, E. J.; Cho, E. J.; Lee, Y. E.; Ji, M. K.; Shin, D. M.; Chung, Y. K.; Lee, E. J. Am. Chem. Soc. 2004, 126, 2680.
68. (b) Song, H. Y.; Joo, J. M.; Kang, J. W.; Kim, D.-S.; Jung, C.-K.; Kwak, H. S.; Park, J. H.; Lee, E.; Hong, C. Y.; Jeong, S.; Jeon, K.; Park, J. H. J. Org. Chem. 2003, 68, 8080.
69. (c) Jeong, E. J.; Kang, E. J.; Sung, L. T.; Hong, S. K.; Lee, E. J. Am. Chem. Soc. 2002, 124, 14655.
70. (d) Lee, E.; Choi, S. J.; Kim, H.; Han, H. O.; Kim, Y. K.; Min, S. J.; Son, S. H.; Lim, S. M.; Jang, W. S. Angew. Chem., Int. Ed. 2002, 41, 176.
71. Lee, E. In Radicals in Organic Synthesis: Applications; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 2, p 303.
72. Nozaki, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1990, 63, 2578.
73. (a) Johansson, R.; Samuelsson, B. J. Chem. Soc., Chem. Commun. 1984, 201.
74. (b) Johansson, R.; Samuelsson, B. J. Chem. Soc., Perkin Trans. 1 1984, 2371.
75. Matsuura, N.; Yashiki, Y.; Nakashima, S.; Maeda, M.; Sasaki, S. Heterocycles 1999, 51, 975.
76. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989.
77. Nicolaou, K. C.; Shi, G.-Q.; Gunzner, J. L.; Gärtner, P.; Yang, Z. J. Am. Chem. Soc. 1997, 119, 5467.
78. 1H NMR analysis (500 MHz) of the mixture.
79. (a) Rubottom, G. M.; Vazquez, M. A.; Pelegrina, D. R. Tetrahedron Lett. 1974, 15, 4319.
80. (b) McCormik, J. P.; Tomasik, W.; Johnson, M. W. Tetrahedron Lett. 1981, 22, 607.
81. Epoxide 40 is available in five steps from geraniol via Sharpless asymmetric epoxidation. See: (a) Hashimoto, M.; Kan, T.; Nozaki, K.; Yanagiya, M.; Shirahama, H.; Matsumoto, T. J. Org. Chem. 1990, 55, 5088.
82. (b) Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765.
83. 2, 0 °C.
84. The present synthetic entry to iodide 7 is two step shorter than an earlier synthesis that used 39a as an exocyclic enol ether coupling partner in the Suzuki-Miyaura coupling.15a Diagram presented
85. Hansen, T. M.; Florence, G. J.; Lugo-Mas, P.; Chen, J.; Abrams, J. N.; Forsyth, C. J. Tetrahedron Lett. 2003, 44, 57.
86. Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1992, 33, 6299.
87. Enol triflate was successfully used in a related coupling reaction: see ref 14e.
88. Some byproducts were isolated, but their structures were not completely determined.
89. Wittig reaction with 2-(triphenylphosphoranylidene)propionaldehyde (toluene, 80 °C) gave a poor yield of enal 82.
90. (a) Noyori, R.; Nishida, I.; Sakata, J.; Nishizawa, M. J. Am. Chem. Soc. 1980, 102, 1223.
91. (b) Scheidt, K. A.; Chen, H.; Follows, B. C.; Chemler, S. R.; Coffey, D. S.; Roush, W. R. J. Org. Chem. 1998, 63, 6436.
92. Treatment of 84 with TBAF (THF, rt) led to unidentified byproducts resulting from competitive decomposition of the allylic alcohol moiety.
93. Scudiero, D. A.; Shoemaker, R. H.; Paull, K. D.; Monks, A.; Tierney, S.; Nofziger, T. H.; Currens, M. J.; Seniff, D.; Boyd, M. R. Cancer Res. 1988, 48, 4827.