Enantioselective synthesis of the spirotryprostatin A scaffold

Tetrahedron

Volumn 67, Issue 52, 2011, Pages 10195-10202

  Antonchick, Andrey P ^a   Schuster, Hannah ^a,b   Bruss, Hanna ^a,b   Schürmann, Markus ^b   Preut, Hans ^b   Rauh, Daniel ^b   Waldmann, Herbert ^a,b  

^a MAX PLANCK INSTITUTE OF MOLECULAR PHYSIOLOGY   (Germany)

^b TU DORTMUND UNIVERSITY   (Germany)

Author keywords

1,3 Dipolar cycloaddition; 3+2 Cycloaddition; All carbon quaternary spirocenter; Biology oriented synthesis; Spirotryprostatin A

Indexed keywords

3 (4 BROMOPHENYL) 5' FLUORO 5A,6,7,8 TETRAHYDRO 1H,5H SPIRO(DIPYRROLO[1,2 A:1',2' D]PYRAZINE 2,3' INDOLE) 2',5,10(1'H,10AH) TRIONE; 3 (4 BROMOPHENYL) 5A,6,7,8 TETRAHYDRO 1H,5H SPIRO(DIPYRROLO[1,2 A:1',2' D]PYRAZINE 2,3' INDOLE) 2',5,10(1'H,10AH) TRIONE; 3,3' PYRROLIDINYLSPIROOXINDOLE DERIVATIVE; 5' FLUORO 3 (4 METHOXYPHENYL) 5A,6,7,8 TETRAHYDRO 1H,5H SPIRO(DIPYRROLO[1,2 A:1',2' D]PYRAZINE 2,3' INDOLE) 2',5,10(1'H,10AH) TRIONE; 5' FLUORO 3 PHENYL 5A,6,7,8 TETRAHYDRO 1H,5H SPIRO(DIPYRROLO[1,2 A:1',2' D]PYRAZINE 2,3' INDOLE) 2',5,10(1'H,10AH) TRIONE; 6' BROMO 3 (4 BROMOPHENYL) 5A,6,7,8 TETRAHYDRO 1H,5H SPIRO(DIPYRROLO[1,2 A:1',2' D]PYRAZINE 2,3' INDOLE) 2',5,10(1'H,10AH) TRIONE; 6' BROMO 3 (4 METHOXYPHENYL) 5A,6,7,8 TETRAHYDRO 1H,5H SPIRO(DIPYRROLO[1,2 A:1',2' D]PYRAZINE 2,3' INDOLE) 2',5,10(1'H,10AH) TRIONE; ALKALOID DERIVATIVE; INDOLE DERIVATIVE; METHYL 1' ACETYL 2 OXO 2' [4 (TRIFLUOROMETHYL)PHENYL] 1,2 DIHYDROSPIRO[INDOLE 3,3' PYRROLIDINE] 5' CARBOXYLATE; METHYL 1' ACETYL 2' (2 BROMO 3 HYDROXY 4 METHOXYPHENYL) 2 OXO 1,2 DIHYDROSPIRO[INDOLE 3,3' PYRROLIDINE] 5' CARBOXYLATE; METHYL 1' ACETYL 2' (2,3 DICHLOROPHENYL) 2 OXO 1,2 DIHYDROSPIRO[INDOLE 3,3' PYRROLIDINE] 5' CARBOXYLATE; METHYL 1' ACETYL 2' (2,3 DICHLOROPHENYL) 5 METHOXY 2 OXO 1,2 DIHYDROSPIRO[INDOLE 3,3' PYRROLIDINE] 5' CARBOXYLATE; METHYL 1' ACETYL 2' (4 BROMOPHENYL) 2 OXO 1,2 DIHYDROSPIRO[INDOLE 3,3' PYRROLIDINE] 5' CARBOXYLATE; METHYL 1' ACETYL 2' (4 BROMOPHENYL) 5 CHLORO 2 OXO 1,2 DIHYDROSPIRO[INDOLE 3,3' PYRROLIDINE] 5' CARBOXYLATE; METHYL 1' ACETYL 2' (4 BROMOPHENYL) 5 FLUORO 2 OXO 1,2 DIHYDROSPIRO[INDOLE 3,3' PYRROLIDINE] 5' CARBOXYLATE; METHYL 1' ACETYL 2' (4 BROMOPHENYL) 5 METHOXY 2 OXO 1,2 DIHYDROSPIRO[INDOLE 3,3' PYRROLIDINE] 5' CARBOXYLATE; METHYL 1' ACETYL 2' (4 CYANOPHENYL) 2 OXO 1,2 DIHYDROSPIRO[INDOLE 3,3' PYRROLIDINE] 5' CARBOXYLATE; METHYL 1' ACETYL 2' (4 METHOXYPHENYL) 2 OXO 1,2 DIHYDROSPIRO[INDOLE 3,3' PYRROLIDINE] 5' CARBOXYLATE; METHYL 1' ACETYL 6 BROMO 2' (4 BROMOPHENYL) 2 OXO 1,2 DIHYDROSPIRO[INDOLE 3,3' PYRROLIDINE] 5' CARBOXYLATE; OXINDOLE; PYRROLIDINE DERIVATIVE; SPIROTRYPROSTATIN A; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CHEMICAL REACTION; CYCLOADDITION; DEPROTECTION REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; ONE POT SYNTHESIS; PRIORITY JOURNAL; REPRODUCIBILITY; RING CLOSING METATHESIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 82255191940     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.04.056     Document Type: Article

References (90)

1. F.E. Koehn, and G.T. Carter Nat. Rev. Drug Discovery 4 2005 206 220
2. K.S. Lam Trends Microbiol. 15 2007 279 289
3. D.J. Newman, and G.M. Cragg J. Nat. Prod. 70 2007 461 477
4. A. Ganesan Curr. Opin. Chem. Biol. 12 2008 306 317
5. A.L. Harvey Drug Discovery Today 13 2008 894 901
6. J.W.H. Li, and J.C. Vederas Science 325 2009 161 165
7. T.F. Molinski, D.S. Dalisay, S.L. Lievens, and J.P. Saludes Nat. Rev. Drug Discovery 8 2009 69 85
8. B. Meseguer, D. Alonso-Diaz, N. Griebenow, T. Herget, and H. Waldmann Angew. Chem., Int. Ed. 38 1999 2902 2906
9. B. Meseguer, D. Alonso-Diaz, N. Griebenow, T. Herget, and H. Waldmann Chem. - Eur. J. 6 2000 3943 3957
10. D. Brohm, S. Metzger, A. Bhargava, O. Muller, F. Lieb, and H. Waldmann Angew. Chem., Int. Ed. 41 2001 307 311
11. D. Brohm, N. Philippe, S. Metzger, A. Bhargava, O. Muller, F. Lieb, and H. Waldmann J. Am. Chem. Soc. 124 2002 13171 13178
12. M.A. Koch, L.O. Wittenberg, S. Basu, D.A. Jeyaraj, E. Gourzoulidou, K. Reinecke, A. Odermatt, and H. Waldmann Proc. Natl. Acad. Sci. U.S.A. 101 2004 16721 16726
13. M.A. Koch, A. Schuffenhauer, M. Scheck, S. Wetzel, M. Casaulta, A. Odermatt, P. Ertl, and H. Waldmann Proc. Natl. Acad. Sci. U.S.A. 102 2005 17272 17277
14. A. Nören-Müller, I. Reis-Correa, H. Prinz, C. Rosenbaum, K. Saxena, H.J. Schwalbe, D. Vestweber, G. Cagna, S. Schunk, O. Schwarz, H. Schiewe, and H. Waldmann Proc. Natl. Acad. Sci. U.S.A. 103 2006 10606 10611
15. A.B. Garcia, T. Lessmann, J.D. Umarye, V. Mamane, S. Sommer, and H. Waldmann Chem. Commun. 2006 3868 3870
16. A. Schuffenhauer, P. Ertl, S. Roggo, S. Wetzel, M.A. Koch, and H. Waldmann J. Chem. Inf. Model. 47 2007 47 58
17. M. Kaiser, S. Wetzel, K. Kumar, and H. Waldmann Cell. Mol. Life Sci. 65 2008 1186 1201
18. H. Waldmann, V. Khedkar, H. Dückert, M. Schürmann, I.M. Oppel, and K. Kumar Angew. Chem., Int. Ed. 47 2008 6869 6872
19. A. Nören-Müller, W. Wilk, K. Saxena, H. Schwalbe, M. Kaiser, and H. Waldmann Angew. Chem., Int. Ed. 47 2008 5973 5977
20. K. Kumar, and H. Waldmann Angew. Chem., Int. Ed. 48 2009 3224 3242
21. S. Renner, W.A.L. van Otterlo, M.D. Seoane, S. Mocklinghoff, B. Hofmann, S. Wetzel, A. Schuffenhauer, P. Ertl, T.I. Oprea, D. Steinhilber, L. Brunsveld, D. Rauh, and H. Waldmann Nat. Chem. Biol. 5 2009 585 592
22. S. Wetzel, K. Klein, S. Renner, D. Rauh, T.I. Oprea, P. Mutzel, and H. Waldmann Nat. Chem. Biol. 5 2009 581 583
23. S. Wetzel, W. Wilk, S. Chammaa, B. Sperl, A.G. Roth, A. Yektaoglu, S. Renner, T. Berg, C. Arenz, A. Giannis, T.I. Oprea, D. Rauh, M. Kaiser, and H. Waldmann Angew. Chem., Int. Ed. 49 2010 3666 3670
24. F.J. Dekker, O. Rocks, N. Vartak, S. Menninger, C. Hedberg, R. Balamurugan, S. Wetzel, S. Renner, M. Gerauer, B. Scholermann, M. Rusch, J.W. Kramer, D. Rauh, G.W. Coates, L. Brunsveld, P.I.H. Bastiaens, and H. Waldmann Nat. Chem. Biol. 6 2010 449 456
25. R.S. Bon, and H. Waldmann Acc. Chem. Res. 43 2010 1103 1114
26. S. Basu, B. Ellinger, S. Rizzo, C. Deraeve, M. Schürmann, H. Preut, H.-D. Arndt, and H. Waldmann Proc. Natl. Acad. Sci. U.S.A. 108 2011 6805 6810
27. J.S. Bindra R.H.F. Manske, The Alkaloids Vol. 14 1973 Academic New York 84 121
28. S. Sakai, N. Aimi, K. Yamaguchi, H. Ohhira, K. Hori, and J. Haginiwa Tetrahedron Lett. 16 1975 715 718
29. N. Aimi, K. Yamaguchi, S. Sakai, J. Haginiwa, and A. Kubo Chem. Pharm. Bull. 26 1978 3444 3449
30. S. Sakai, N. Aimi, K. Yamaguchi, E. Yamanaka, and J. Haginiwa J. Chem. Soc., Perkin Trans. 1 1982 1257 1262
31. W.H. Wong, P.B. Lim, and C.H. Chuah Phytochemistry 41 1996 313 315
32. C. Pellegrini, M. Weber, and H.J. Borschberg Helv. Chim. Acta 79 1996 151 168
33. N. Anderton, P.A. Cockrum, S.M. Colegate, J.A. Edgar, K. Flower, I. Vit, and R.I. Willing Phytochemistry 48 1998 437 439
34. R. Reyes-Chilpa, J. Rivera, M. Oropeza, P. Mendoza, B. Amekraz, C. Jankowski, and M. Campos Biol. Pharm. Bull. 27 2004 1617 1620
35. T.S. Kam, and Y.M. Choo Tetrahedron 56 2000 6143 6150
36. J. Ma, and S.M. Hecht Chem. Commun. 2004 1190 1191
37. R. Pandey, S.C. Singh, and M.M. Gupta Phytochemistry 67 2006 2164 2169
38. C.B. Cui, H. Kakeya, and H. Osada Tetrahedron 52 1996 12651 12666
39. C.B. Cui, H. Kakeya, and H. Osada J. Antibiot. 49 1996 832 835
40. F.Z. Wang, Y.C. Fang, T.J. Zhu, M. Zhang, A.Q. Lin, Q.Q. Gu, and W.M. Zhu Tetrahedron 64 2008 7986 7991
41. S. Edmondson, S.J. Danishefsky, L. Sepp-Lorenzino, and N. Rosen J. Am. Chem. Soc. 121 1999 2147 2155
42. A.P. Antonchick, C. Gerding-Reimers, M. Catarinella, M. Schürmann, H. Preut, S. Ziegler, D. Rauh, and H. Waldmann Nat. Chem. 2 2010 735 740
43. For a review on the challenge of developing catalytic asymmetric methods for the synthesis of quaternary all-carbon centers, see: E.J. Corey, and A. Guzman-Perez Angew. Chem., Int. Ed. 37 1998 388 401
44. C.J. Douglas, and L.E. Overman Proc. Natl. Acad. Sci. U.S.A. 101 2004 5363 5367
45. B.M. Trost, and C.H. Jiang Synthesis 2006 369 396
46. P.G. Cozzi, R. Hilgraf, and N. Zimmermann Eur. J. Org. Chem. 2007 5969 5994
47. A. Steven, and L.E. Overman Angew. Chem., Int. Ed. 46 2007 5488 5508
48. B.M. Trost, and M.K. Brennan Synthesis 2009 3003 3025
49. For excellent reviews on the synthesis of 3,3′-pyrrolidinyl- spirooxindoles, see: C. Marti, and E.M. Carreira Eur. J. Org. Chem. 2003 2209 2219
50. C.V. Galliford, and K.A. Scheidt Angew. Chem., Int. Ed. 46 2007 8748 8758
51. S.D. Edmondson, and S.J. Danishefsky Angew. Chem., Int. Ed. 37 1998 1138 1140
52. M. Ito, C.W. Clark, M. Mortimore, J.B. Goh, and S.F. Martin J. Am. Chem. Soc. 123 2001 8003 8010
53. X.Z. Wearing, and J.M. Cook Org. Lett. 4 2002 4237 4240
54. H. Takayama, R. Fujiwara, Y. Kasai, M. Kitajima, and N. Aimi Org. Lett. 5 2003 2967 2970
55. C.M. Li, C. Chan, A.C. Heimann, and S.J. Danishefsky Angew. Chem., Int. Ed. 46 2007 1444 1447
56. F. von Nussbaum, and S.J. Danishefsky Angew. Chem., Int. Ed. 39 2000 2175 2178
57. F.Y. Miyake, K. Yakushijin, and D.A. Horne Angew. Chem., Int. Ed. 43 2004 5357 5360
58. P.R. Sebahar, and R.M. Williams J. Am. Chem. Soc. 122 2000 5666 5667
59. P.R. Sebahar, H. Osada, T. Usui, and R.M. Williams Tetrahedron 58 2002 6311 6322
60. T. Onishi, P.R. Sebahar, and R.M. Williams Org. Lett. 5 2003 3135 3137
61. M.M.C. Lo, C.S. Neumann, S. Nagayama, E.O. Perlstein, and S.L. Schreiber J. Am. Chem. Soc. 126 2004 16077 16086
62. C.V. Galliford, J.S. Martenson, C. Stern, and K.A. Scheidt Chem. Commun. 2007 631 633
63. H.C. Malinakova, and L.S. Liebeskind Org. Lett. 2 2000 4083 4086
64. L.E. Overman, and M.D. Rosen Angew. Chem., Int. Ed. 39 2000 4596 4599
65. G. Lakshmaiah, T. Kawabata, M.H. Shang, and K. Fuji J. Org. Chem. 64 1999 1699 1704
66. T.D. Bagul, G. Lakshmaiah, T. Kawabata, and K. Fuji Org. Lett. 4 2002 249 251
67. P.B. Alper, C. Meyers, A. Lerchner, D.R. Siegel, and Carreira Angew. Chem., Int. Ed. 38 1999 3186 3189
68. A. Lerchner, and E.M. Carreira J. Am. Chem. Soc. 124 2002 14826 14827
69. C. Meyers, and E.M. Carreira Angew. Chem., Int. Ed. 42 2003 694 696
70. C. Marti, and E.M. Carreira J. Am. Chem. Soc. 127 2005 11505 11515
71. B.M. Trost, and D.T. Stiles Org. Lett. 9 2007 2763 2766
72. For recent reviews on asymmetric [3+2] cycloaddition of azomethine ylides, see: C. Najera, and J.M. Sansano Angew. Chem., Int. Ed. 44 2005 6272 6276
73. G. Pandey, P. Banerjee, and S.R. Gadre Chem. Rev. 106 2006 4484 4517
74. Pellissier Tetrahedron 63 2007 3235 3285
75. M. Naodovic, and H. Yamamoto Chem. Rev. 108 2008 3132 3148
76. N.T. Patil, and Y. Yamamoto Chem. Rev. 108 2008 3395 3442
77. L.M. Stanley, and M.P. Sibi Chem. Rev. 108 2008 2887 2902
78. For recent results on asymmetric [3+2] cycloaddition of azomethine ylides, see: X.H. Chen, W.Q. Zhang, and L.Z. Gong J. Am. Chem. Soc. 130 2008 5652 5653
79. S.I. Fukuzawa, and H. Oki Org. Lett. 10 2008 1747 1750
80. A. Lopez-Perez, J. Adrio, and J.C. Carretero J. Am. Chem. Soc. 130 2008 10084 10085
81. C. Najera, M.D. Retamosa, and J.M. Sansano Angew. Chem., Int. Ed. 47 2008 6055 6058
82. C.J. Wang, G. Liang, Z.Y. Xue, and F. Gao J. Am. Chem. Soc. 130 2008 17250 17251
83. J. Hernandez-Toribio, R.G. Arrayas, B. Martin-Matute, and J.C. Carretero Org. Lett. 11 2009 393 396
84. A. Lopez-Perez, J. Adrio, and A.C. Carretero Angew. Chem., Int. Ed. 48 2009 340 343
85. X.H. Chen, Q. Wei, S.W. Luo, H. Xiao, and L.Z. Gong J. Am. Chem. Soc. 131 2009 13819 13825
86. T. Arai, A. Mishiro, N. Yokoyama, K. Suzuki, and H. Sato J. Am. Chem. Soc. 132 2010 5338 5339
87. S. Cabrera, R.G. Arrayas, and J.C. Carretero J. Am. Chem. Soc. 127 2005 16394 16395 And with methyl methacrylate
88. H.Y. Kim, H.J. Shih, W.E. Knabe, and K. Oh Angew. Chem., Int. Ed. 48 2009 7420 7423
89. E. Wenkert, J.H. Udelhofen, and N.K. Bhattacharyya J. Am. Chem. Soc. 81 1959 3763 3768
90. J.C. Seaton, M.D. Nair, O.E. Edwards, and L. Marion Can. J. Chem. 38 1960 1035 1042