Total syntheses of bryostatins: Synthesis of two ring-expanded bryostatin analogues and the development of a new-generation strategy to access the C7-C27 fragment

Chemistry - A European Journal

Volumn 17, Issue 35, 2011, Pages 9789-9805

  Trost, Barry M ^a   Yang, Hanbiao ^a   Dong, Guangbin ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

bryostatins; domino reactions; metathesis; palladium; ruthenium

Indexed keywords

ANTICANCER ACTIVITIES; BRYOSTATINS; CANCER CELL LINES; DOMINO REACTIONS; ENYNE COUPLING; LATE STAGE; MACROCYCLES; METATHESIS; RING CLOSING METATHESIS; TOTAL SYNTHESIS;

CELL CULTURE; OLEFINS; REACTION KINETICS; RUTHENIUM;

PLANNING;

ANTINEOPLASTIC AGENT; BRYOSTATIN; CYCLOALKANE DERIVATIVE; MACROLIDE; PALLADIUM; RUTHENIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; HUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; BRYOSTATINS; CATALYSIS; CELL LINE, TUMOR; CYCLIZATION; CYCLOPARAFFINS; HUMANS; MACROLIDES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PALLADIUM; RUTHENIUM; STEREOISOMERISM;

EID: 80051749705     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201002932     Document Type: Article

References (96)

1. For a preliminary report of a portion of our work, see:, B. M. Trost, H. Yang, O. R. Thiel, A. J. Frontier, C. S. Brindle, J. Am. Chem. Soc. 2007, 129, 2206-2207
2. for our synthesis of bryostatin rings A and B, see: B. M. Trost, H. Yang, C. S. Brindle, G. Dong, Chem. Eur. J. 2011, 17, 9777-9788
3. for our synthesis of bryostatin ring C, see: B. M. Trost, A. J. Frontier, O. R. Thiel, H. Yang, G. Dong, Chem. Eur. J. 2011, 17, 9762-9776.
4. For bryostatin isolation and structure determination, see: bryostatin 1
5. G. R. Pettit, C. L. Herald, D. L. Doubek, D. L. Herald, E. Arnold, J. Clardy, J. Am. Chem. Soc. 1982, 104, 6846-6848; bryostatin 2
6. G. R. Pettit, C. L. Herald, Y. Kamano, D. Gust, R. Aoyagi, J. Nat. Prod. 1983, 46, 528-531; bryostatins 1-3
7. G. R. Pettit, C. L. Herald, Y. Kamano, J. Org. Chem. 1983, 48, 5354-5356; bryostatin 3
8. D. E. Schaufelberger, G. N. Chmurny, J. A. Beutler, M. P. Koleck, A. B. Alvarado, B. W. Schaufelberger, G. M. Muschik, J. Org. Chem. 1991, 56, 2895-2900
9. G. N. Chmurny, M. P. Koleck, B. D. Hilton, J. Org. Chem. 1992, 57, 5260-5264; bryostatin 4
10. G. R. Pettit, Y. Kamano, C. L. Herald, M. Tozawa, J. Am. Chem. Soc. 1984, 106, 6768-6771; bryostatins 5-7
11. G. R. Pettit, Y. Kamano, C. L. Herald, M. Tozawa, Can. J. Chem. 1985, 63, 1204-1208; bryostatin 8
12. G. R. Pettit, Y. Kamano, R. Aoyagi, C. L. Herald, D. L. Doubek, J. M. Schmidt, J. J. Rudloe, Tetrahedron 1985, 41, 985-994; bryostatin 9
13. G. R. Pettit, Y. Kamano, C. L. Herald, J. Nat. Prod. 1986, 49, 661-664; bryostatins 10 and 11
14. G. R. Pettit, Y. Kamano, C. L. Herald, J. Org. Chem. 1987, 52, 2848-2854; bryostatins 12 and 13
15. G. R. Pettit, J. E. Leet, C. L. Herald, Y. Kamano, F. E. Boettner, L. Baczynskyj, R. A. Nieman, J. Org. Chem. 1987, 52, 2854-2860; bryostatins 14 and 15
16. G. R. Pettit, F. Gao, D. Sengupta, J. C. Coll, C. L. Herald, D. L. Doubek, J. M. Schmidt, J. R. Van Camp, J. J. Rudloe, R. A. Nieman, Tetrahedron 1991, 47, 3601-3614; bryostatins 16-18
17. G. R. Pettit, F. Gao, P. M. Blumberg, C. L. Herald, J. C. Coll, Y. Kamano, N. E. Lewin, J. M. Schmidt, J. C. Chapuis, J. Nat. Prod. 1996, 59, 286-289; bryostatin 19
18. H. Lin, X. Yao, Y. Yi, X. Li, H. Wu, Zhongguo Haiyang Yaowu 1998, 17, 1-6; bryostatin 20
19. N. Lopanik, K. R. Gustafson, N. Lindquist, J. Nat. Prod. 2004, 67, 1412-1414.
20. For recent reviews, see:, K. J. Hale, S. Manaviazar, Chem. Asian J. 2010, 5, 704-754, and references therein.
21. For the total synthesis of bryostatins, see
22. bryostatin 7:, M. Kageyama, T. Tamura, M. H. Nantz, J. C. Roberts, P. Somfai, D. C. Whritenour, S. Masamune, J. Am. Chem. Soc. 1990, 112, 7407-7408, and references therein
23. bryostatin 2:, D. A. Evans, P. H. Carter, E. M. Carreira, A. B. Charette, J. A. Prunet, M. Lautens, J. Am. Chem. Soc. 1999, 121, 7540-7552, and references therein
24. bryostatin 3:, K. Ohmori, Y. Ogawa, T. Obitsu, Y. Ishikawa, S. Nishiyama, S. Yamamura, Angew. Chem. 2000, 112, 2376-2379
25. Angew. Chem. Int. Ed. 2000, 39, 2290-2294, and references therein
26. bryostatin 16:, B. M. Trost, G. Dong, Nature 2008, 456, 485-488
27. for a formal synthesis of bryostatin 7, see:, S. Manaviazar, M. Frigerio, G. S. Bhatia, M. G. Hummersone, A. E. Aliev, K. J. Hale, Org. Lett. 2006, 8, 4477-4480, and references therein.
28. For the synthesis of bryostatin analogues, see
29. P. A. Wender, B. A. DeChristopher, A. J. Schrier, J. Am. Chem. Soc. 2008, 130, 6658-6659, and references therein
30. G. E. Keck, Y. B. Pondel, A. Rudra, J. C. Stephens, N. Kedei, N. E. Lewin, M. L. Peach, P. M. Blumberg, Angew. Chem. 2010, 122, 4684-4688
31. Angew. Chem. Int. Ed. 2010, 49, 4580-4584, and references therein.
32. For recent work on bryostatins, see
33. Y. Lu, M. J. Krische, Org. Lett. 2009, 11, 3108-3111
34. E. A. Voight, H. Seradj, P. A. Roethles, S. D. Burke, Org. Lett. 2004, 6, 4045-4048
35. A. Vakalopoulos, T. F. J. Lampe, H. M. R. Hoffmann, Org. Lett. 2001, 3, 929-932
36. S. Kiyooka, H. Maeda, Tetrahedron: Asymmetry 1997, 8, 3371.
37. K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem. 2005, 117, 4564-4601
38. Angew. Chem. Int. Ed. 2005, 44, 4490-4527
39. J. B. Brenneman, S. F. Martin, Curr. Org. Chem. 2005, 9, 1535-1549
40. S. F. Martin, Pure Appl. Chem. 2005, 77, 1207-1212
41. R. H. Grubbs, T. M. Trnka, in Ruthenium in Organic Synthesis (Ed.:, S.-H. Murahashi,), Wiley-VCH, Weinheim, 2004, pp. 153-177
42. A. H. Hoveyda, R. R. Schrock, in Organic Synthesis Highlights V (Eds.:, H-G Schmalz, T. Wirth,), Wiley-VCH, Weinheim, 2003, pp. 210-229.
43. The synthesis of compound 5 was described in our previous paper, see Reference [1c].
44. B. M. Trost, H. Yang, G. Wuitschik, Org. Lett. 2005, 7, 4761-4764.
45. M. V. N. De Souza, Mini-Rev. Org. Chem. 2006, 3, 155-165.
46. P. R. Blakemore, C. C. Browder, J. Hong, C. M. Lincoln, P. A. Nagornyy, L. A. Robarge, D. J. Wardrop, J. D. White, J. Org. Chem. 2005, 70, 5449-5460.
47. I. Shiina, J. Shibata, R. Ibuka, Y. Imai, T. Mukaiyama, Bull. Chem. Soc. Jpn. 2001, 74, 113-122.
48. For the use of a similar Mukaiyama reaction/anti-reduction to construct the bryostatin C1-C7 fragment, see reference [4b].
49. D. A. Evans, K. T. Chapman, E. M. Carreira, J. Am. Chem. Soc. 1988, 110, 3560-3578.
50. A. McCluskey, I. W. M. Muntari, D. J. Young, J. Org. Chem. 2001, 66, 7811-7817.
51. V. Nair, S. Ros, C. N. Jayan, B. S. Pillai, Tetrahedron 2004, 60, 1959-1982.
52. J. Otera, S. Ioka, H. Nozaki, J. Org. Chem. 1989, 54, 4013-4014
53. J. Otera, T. Yano, A. Kawabata, H. Nozaki, Tetrahedron Lett. 1986, 27, 2383-2386.
54. P. A. Bartlett, W. S. Johnson, Tetrahedron Lett. 1970, 11, 4459-4462.
55. K. C. Nicolaou, A. A. Estrada, M. Zak, S. H. Lee, B. S. Safina, Angew. Chem. 2005, 117, 1402-1406
56. Angew. Chem. Int. Ed. 2005, 44, 1378-1382.
57. F.-L. Qing, X.-J. Yue, Tetrahedron Lett. 1997, 38, 8067-8070.
58. Product 37 was not stable under the reaction conditions due to the migration of the C20 acetate to the C17 hydroxyl group.
59. N. A. Petasis, E. I. Bzowej, J. Am. Chem. Soc. 1990, 112, 6392-6394.
60. I. Shiina, M. Kubota, H. Oshiumi, M. Hashizume, J. Org. Chem. 2004, 69, 1822-1830
61. I. Shiina, M. Kubota, R. Ibuka, Tetrahedron Lett. 2002, 43, 7535-7539
62. I. Shiina, R. Ibuka, M. Kubota, Chem. Lett. 2002, 286-287.
63. The reaction was clean by TLC analysis; the fate of the rest of acid 36 was not clear.
64. S. B. Garber, J. S. Kingsbury, B. L. Gray, A. H. Hoveyda, J. Am. Chem. Soc. 2000, 122, 8168-8179.
65. J. C. Conrad, H. H. Parnas, J. L. Snelgrove, D. E. Fogg, J. Am. Chem. Soc. 2005, 127, 11882-11883.
66. M. Ball, B. J. Bradshaw, R. Dumeunier, T. J. Gregson, S. MacCormick, H. Omori, E. J. Thomas, Tetrahedron Lett. 2006, 47, 2223-2227.
67. T. R. Hoye, C. S. Jeffrey, M. A. Tennakoon, J. Wang, H. Zhao, J. Am. Chem. Soc. 2004, 126, 10210-10211; this strategy was later used by Wang and Porco et al. in their total synthesis of oximidine III, see
68. X. Wang, E. J. Bowman, B. J. Bowman, J. A. Porco, Jr., Angew. Chem. 2004, 116, 3685-3689
69. Angew. Chem. Int. Ed. 2004, 43, 3601-3605.
70. T. Okazoe, K. Takai, K. Utimoto, J. Am. Chem. Soc. 1987, 109, 951-953.
71. A. K. Chatterjee, T.-L. Choi, D. P. Sanders, R. H. Grubbs, J. Am. Chem. Soc. 2003, 125, 11360-11370.
72. K. Takai, K. Nitta, K. Utimoto, J. Am. Chem. Soc. 1986, 108, 7408-7410.
73. E.-i. Negishi, X. Zeng, Z. Tan, M. Qian, Q. Hu, Z. Huang, in Metal-Catalyzed Cross-Coupling Reactions, 2 nd ed., (Eds.: A. de Meijere, F. Diederich,), Wiley-VCH, Weinheim, 2004, pp. 815-889
74. E. Negishi, Acc. Chem. Res. 1982, 15, 340-348.
75. B. R. Hearn, D. Zhang, Y. Li, D. C. Myles, Org. Lett. 2006, 8, 3057
76. S. J. Shaw, K. F. Sundermann, M. A. Burlingame, D. C. Myles, B. S. Freeze, M. Xian, I. Brouard, A. B. Smith III, J. Am. Chem. Soc. 2005, 127, 6532.
77. For a recent review, see:, B. M. Trost, M. U. Frederiksen, M. T. Rudd, Angew. Chem. 2005, 117, 6788-6825
78. Angew. Chem. Int. Ed. 2005, 44, 6630-6666.
79. This was adapted from a procedure reported earlier by Wender et al., see:, P. A. Wender, J. L. Baryza, C. E. Bennett, F. C. Bi, S. E. Brenner, M. O. Clarke, J. C. Horan, C. Kan, E. Lacôte, P. G. Nell, T. M. Turner, J. Am. Chem. Soc. 2002, 124, 13648-13649.
80. M-;J. Lin, T-P. Loh, J. Am. Chem. Soc. 2003, 125, 13042-13043.
81. High quality Dess-Martin periodinane was required for this oxidation; for Dess-Martin oxidation, see:, D. B. Dess, J. C. Martin, J. Am. Chem. Soc. 1991, 113, 7277-7287.
82. For a review, see:, E. J. Corey, J. C. Helal, Angew. Chem. 1998, 110, 2092-2118
83. Angew. Chem. Int. Ed. 1998, 37, 1986-2012.
84. Ketone 77 decomposed when treated with silica gel.
85. For reviews, see
86. W. S. Wadsworth, Jr., Org. React. 1977, 25, 73-253
87. J. Boutagy, R. Thomas, Chem. Rev. 1974, 74, 87-99
88. S. E. Kelly, Compt. Org. Syn. 1991, 1, 729-817
89. B. E. Maryanoff, A. B. Reitz, Chem. Rev. 1989, 89, 863-927.
90. Formation of some uncyclized product was observed.
91. G. J. Roth, B. Liepold, S. G. Müller, H. J. Bestmann, Synthesis 2004, 59-62.
92. B. M. Trost, A. J. Frontier, J. Am. Chem. Soc. 2000, 122, 11727-11728.
93. For gold-catalyzed 5-exo cyclization with alcohols as nucleophiles, see
94. Y. Liu, F. Song, Z. Song, M. Liu, B. Yan, Org. Lett. 2005, 7, 5409-5412; for cationic gold-catalyzed ketal formation, see
95. B. Liu, J. K. De Brabander, Org. Lett. 2006, 8, 4907-4910.
96. For a recent review on gold catalysis, see:, J. Muzart, Tetrahedron 2008, 64, 5815-5849.