Stereoselective β-C-glycosylation by a palladium-catalyzed decarboxylative allylation: Formal synthesis of aspergillide A

Angewandte Chemie - International Edition

Volumn 52, Issue 19, 2013, Pages 5134-5137

  Zeng, Jing ^a   Ma, Jimei ^a   Xiang, Shaohua ^a   Cai, Shuting ^a   Liu, Xue Wei ^a  

^a Nanyang Technological University   (Singapore)

Author keywords

aspergillide A; C glycosylation; decarboxylative allylation; glycals; palladium

Indexed keywords

ASPERGILLIDE A; C-GLYCOSYLATION; DIASTEREO-SELECTIVITY; FORMAL SYNTHESIS; GLYCALS; PALLADIUM-CATALYZED; PROTECTING GROUP; STEREO-SELECTIVE;

ALLYLATION; GLYCOSYLATION; KETONES; ORGANOMETALLICS; PALLADIUM; STEREOSELECTIVITY;

ESTERIFICATION;

ALLYL COMPOUND; ASPERGILLIDE A; MACROLIDE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; DECARBOXYLATION; GLYCOSYLATION; STEREOISOMERISM; SYNTHESIS;

ALLYL COMPOUNDS; CATALYSIS; DECARBOXYLATION; GLYCOSYLATION; MACROLIDES; MOLECULAR STRUCTURE; PALLADIUM; STEREOISOMERISM;

EID: 84877703204     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201210266     Document Type: Article

References (103)

1. M. H. D. Postema, Tetrahedron 1992, 48, 8545
2. Y. Du, R. J. Linhardt, I. R. Vlahov, Tetrahedron 1998, 54, 9913
3. K. C. Nicolaou, H. J. Mitchell, Angew. Chem. 2001, 113, 1624
4. Angew. Chem. Int. Ed. 2001, 40, 1576
5. L. Somsák, Chem. Rev. 2001, 101, 81.
6. R. J. Ferrier, J. Chem. Soc. C 1964, 5443
7. R. J. Ferrier, D. M. Ciment, J. Chem. Soc. C 1966, 441
8. R. J. Ferrier, N. Prasad, J. Chem. Soc. Chem. Commun. 1968, 476
9. R. J. Ferrier, Adv. Carbohydr. Chem. Biochem. 1969, 24, 199
10. R. J. Ferrier, N. Prasad, J. Chem. Soc. C 1969, 570.
11. A. Agarwal, S. Rani, Y. D. Vankar, J. Org. Chem. 2004, 69, 6137
12. J. L. Badu, A. Khare, Y. D. Vankar, Molecules 2005, 10, 884
13. D. D. David, O. M. Pedro, I. P. Juan, S. M. Victor, Curr. Org. Chem. 2006, 10, 457
14. P. Nagaraj, N. G. Ramesh, Tetrahedron Lett. 2009, 50, 3970.
15. R. D. Dawe, B. Fraser-Reid, J. Chem. Soc. Chem. Commun. 1981, 1180
16. S. Danishefsky, J. F. Kerwin, J. Org. Chem. 1982, 47, 3803
17. D. P. Steinhuebel, J. J. Fleming, J. DuBois, Org. Lett. 2002, 4, 293
18. A. S. Vieira, P. F. Fiorante, T. L. S. Hough, F. P. Ferreira, Lüdtke, H. L. A. Stefani, Org. Lett. 2008, 10, 5215
19. R. D. S. Balamurugan, S. R. Koppolu, Tetrahedron 2009, 65, 8139.
20. J. Ramnauth, O. Poulin, S. Rakhit, S. P. Maddaford, Org. Lett. 2001, 3, 2013
21. D.-C. Xiong, L.-H. Zhang, X.-S. Ye, Org. Lett. 2009, 11, 1709
22. H.-H. Li, X.-S. Ye, Org. Biomol. Chem. 2009, 7, 3855
23. M. Lei, L. Gao, J.-S. Yang, Tetrahedron Lett. 2009, 50, 5135
24. S. Xiang, S. Cai, J. Zeng" X.-W. Liu, Org. Lett. 2011, 13, 4608
25. Y. Bai, M. Leow, J. Zeng, X.-W. Liu, Org. Lett. 2011, 13, 5648.
26. A. Pfaltz, M. Lautens, in Comprehensive Asymmetric Catalysis, Vol.2 (Eds.:, E.N. Jacobsen, A. Pfaltz, H. Yamamoto,), Springer, New York, 1999, p. 833
27. B. M. Trost, Chem. Pharm. Bull. 2002, 50, 1
28. B. M. Trost, M. L. Crawley, Chem. Rev. 2003, 103, 2921
29. O. Belda, C. Moberg, Acc. Chem. Res. 2004, 37, 159
30. B. M. Trost, J. Org. Chem. 2004, 69, 5813
31. H. Miyabe, Y. Takemoto, Synlett 2005, 1641
32. B. M. Trost, D. R. Fandrick, Aldrichimica Acta 2007, 40, 59
33. Z. Lu, S. Ma, Angew. Chem. 2008, 120, 264
34. Angew. Chem. Int. Ed. 2008, 47, 258
35. J. F. Hartwig, L. M. Stanley, Acc. Chem. Res. 2010, 43, 1461.
36. B. M. Trost, F. W. Gowland, J. Org. Chem. 1979, 44, 3448
37. L. V. Dunkerton, A. J. Serino, J. Org. Chem. 1982, 47, 2812
38. T. V. RajanBabu, J. Org. Chem. 1985, 50, 3642.
39. R. S. Babu, G. A. O'Doherty, J. Am. Chem. Soc. 2003, 125, 12406
40. A. C. Comely, R. Eelkema, A. J. Minnaard, B. L. Feringa, J. Am. Chem. Soc. 2003, 125, 8714
41. H. Kim, H. Men, C. Lee, J. Am. Chem. Soc. 2004, 126, 1336
42. B. P. Schuff, G. J. Mercer, H. M. Nguyen, Org. Lett. 2007, 9, 3173.
43. B. A. Arndtsen, R. G. Bergman, T. A. Mobley, T. H. Peterson, Acc. Chem. Res. 1995, 28, 154
44. X. Chen, K. M. Engle, D.-H. Wang, J.-Q. Yu, Angew. Chem. 2009, 121, 5196
45. Angew. Chem. Int. Ed. 2009, 48, 5094
46. D. A. Colby, R. G. Bergman, J. A. Ellman, Chem. Rev. 2010, 110, 624
47. I. A. I. Mkhalid, J. H. Barnard, T. B. Marder, J. M. Murphy, J. F. Hartwig, Chem. Rev. 2010, 110, 890
48. T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147.
49. T. Tsuda, Y. Chujo, S. Nishi, K. Tawara, T. Saegusa, J. Am. Chem. Soc. 1980, 102, 6381
50. I. Shimizu, T. Yamada, J. Tsuji, Tetrahedron Lett. 1980, 21, 3199
51. J. Tsuji, I. Minami, Acc. Chem. Res. 1987, 20, 140
52. J. Tsuji, T. Yamada, I. Minami, M. Yuhara, M. Nisar, I. Shimizu, J. Org. Chem. 1987, 52, 2988.
53. S.-L. You, L.-X. Dai, Angew. Chem. 2006, 118, 5372
54. Angew. Chem. Int. Ed. 2006, 45, 5246
55. J. T. Mohr, B. M. Stoltz, Chem. Asian J. 2007, 2, 1476
56. J. T. Mohr, D. C. Ebner, B. M. Stoltz, Org. Biomol. Chem. 2007, 5, 3571
57. M. Austeri, F. Buron, S. Constant, J. Lacour, D. Linder, J. Muller, S. Tortoioli, Pure Appl. Chem. 2008, 80, 967
58. J. D. Weaver, A. Recio, A. J. Grenning, J. A. Tunge, Chem. Rev. 2011, 111, 1846.
59. E. C. Burger, J. A. Tunge, Org. Lett. 2004, 6, 2603
60. R. R. P. Torregrosa, Y. Ariyarathna, K. Chattopadhyay, J. A. Tunge, J. Am. Chem. Soc. 2010, 132, 9280
61. J. D. Weaver, B. J. Ka, D. K. Morris, W. Thompson, J. A. Tunge, J. Am. Chem. Soc. 2010, 132, 12179
62. R. Jana, J. J. Partridge, J. A. Tunge, Angew. Chem. 2011, 123, 5263
63. Angew. Chem. Int. Ed. 2011, 50, 5157.
64. B. M. Trost, J. Xu, J. Am. Chem. Soc. 2005, 127, 17180
65. B. M. Trost, R. N. Bream, J. Xu, Angew. Chem. 2006, 118, 3181
66. Angew. Chem. Int. Ed. 2006, 45, 3109
67. B. M. Trost, J. Xu, T. Schmidt, J. Am. Chem. Soc. 2009, 131, 18343
68. B. M. Trost, B. Schaffner, M. Osipov, D. A. A. Wilton, Angew. Chem. 2011, 123, 3610
69. Angew. Chem. Int. Ed. 2011, 50, 3548.
70. D. C. Behenna, B. M. Stoltz, J. Am. Chem. Soc. 2004, 126, 15044
71. N. H. Sherden, D. C. Behenna, S. C. Virgil, B. M. Stoltz, Angew. Chem. 2009, 121, 6972
72. Angew. Chem. Int. Ed. 2009, 48, 6840
73. D. C. Behenna, Y. Liu, T. Yurino, J. Kim, D. E. White, S. C. Virgil, B. M. Stoltz, Nat. Chem. 2012, 4, 130.
74. M. Nakamura, A. Hajra, K. Endo, E. Nakamura, Angew. Chem. 2005, 117, 7414
75. Angew. Chem. Int. Ed. 2005, 44, 7248
76. N. T. Patil, Z. B. Huo, Y. Yamamoto, J. Org. Chem. 2006, 71, 6991
77. D. Imao, A. Itoi, A. Yamazaki, M. Shirakura, R. Ohtoshi, K. Ogata, Y. Ohmori, T. Ohta, Y. Ito, J. Org. Chem. 2007, 72, 1652
78. S. B. J. Kan, R. Matsubara, F. Berthiol, S. Kobayashi, Chem. Commun. 2008, 6354
79. W. H. Fields, A. K. Khan, M. Sabat, J. J. Chruma, Org. Lett. 2008, 10, 5131
80. A. A. Yeagley, M. A. Lowder, J. J. Chruma, Org. Lett. 2009, 11, 4022
81. D. Linder, M. Austeri, J. Lacour, Org. Biomol. Chem. 2009, 7, 4057
82. J. Wang, Z. Cui, Y. Zhang, H. Li, L. Wu, Z. Liu, Org. Biomol. Chem. 2011, 9, 663.
83. J. Zeng, S. Vedachalam, S. Xiang, X.-W. Liu, Org. Lett. 2011, 13, 42
84. B. K. Gorityala, J. Ma, K. K. Pasunooti, S. Cai, X.-W. Liu, Green Chem. 2011, 13, 573
85. S. Cai, S. Xiang, J. Zeng, B. K. Gorityala, X.-W. Liu, Chem. Commun. 2011, 47, 8676.
86. M. F. Carroll, J. Chem. Soc. 1940, 704
87. M. F. Carroll, J. Chem. Soc. 1940, 1266
88. M. F. Carroll, J. Chem. Soc. 1941, 507
89. W. Kimel, A. C. Cope, J. Am. Chem. Soc. 1943, 65, 1992.
90. E. Keinan, Z. Roth, J. Org. Chem. 1983, 48, 1769, and Ref.[11e].
91. J. A. Keith, D. C. Behenna, J. T. Mohr, S. Ma, S. C. Marinescu, J. Oxgaard, B. M. Stoltz, W. A. Goddard, J. Am. Chem. Soc. 2007, 129, 11876
92. S.-L. Zhang, Y Fu, R. Guo, Q.-X. Shang, L. Liu, J. Am. Chem. Soc. 2010, 132, 638; for calculational studies of the Claisen rearrangement on a sugar scaffold, see
93. S. Gül, F. Schoenebeck, V. Aviyente, K. N. Houk, J. Org. Chem. 2010, 75, 2115.
94. K. Kito, R. Ookura, S. Yoshida, M. Namikoshi, T. Ooi, T. Kusumi, Org. Lett. 2008, 10, 225
95. R. Ookura, K. Kito, Y. Saito, T. Kusumi, T. Ooi, Chem. Lett. 2009, 38, 384.
96. J. Inanaga, K. Hirata, H. Saeki, T. Katsuki, M. Yamaguchi, Bull. Chem. Soc. Jpn. 1979, 52, 1989
97. Y. Kawanami, Y. Dainobu, J. Inanaga, T. Katsuki, M. Yamaguchi, Bull. Chem. Soc. Jpn. 1981, 54, 943.
98. H. Fuwa, A. Saito, M. Sasaki, Angew. Chem. 2010, 122, 3105
99. Angew. chem. Int. Ed. 2010, 49, 3041
100. D. Webb, A. vandenHeuvel, M. Kögl, S. V. Ley, Synlett 2009, 2320
101. S. H. Hong, D. P. Sanders, C. W. Lee, R. H. Grubbs, J. Am. Chem. Soc. 2005, 127, 17160.
102. Compound 8 has been reported to have the best cytotoxic activity among the naturally occurring aspergillides and their analogues:, S. Díaz-Oltra, C. A. Angulo-Pachõn, J. Murga, E. Falomir, M. Carda, J. A. Marco, Chem. Eur. J. 2011, 17, 675.
103. S. Díaz-Oltra, C. A. Angulo-Pachõn, J. Murga, M. Carda, J. A. Marco, J. Org. Chem. 2010, 75, 1775.