Target cum flexibility: Synthesis of C(3′)-spiroannulated nucleosides

Tetrahedron Letters

Volumn 52, Issue 36, 2011, Pages 4627-4630

  Dushing, Mangesh P ^a   Ramana, C V ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

2+2+2 Cyclotrimerization; Dihydroisobenzofuran; Modified nucleosides; Tanaka catalyst; Willkinson catalyst

Indexed keywords

ALKYNE DERIVATIVE; FURAN; NUCLEOSIDE DERIVATIVE;

ANNULATION REACTION; ARTICLE; CHEMICAL REACTION; CYCLOTRIMERIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; MOLECULAR LIBRARY; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 79961168956     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.06.100     Document Type: Article

References (72)

1. For selected reviews on sugar modification in nucleosides, see: C. Wilson, and A.D. Keefe Curr. Opin. Chem. Biol. 10 2006 607 614
2. D.R. Corey J. Clin. Invest. 117 2007 3615 3622
3. A.J.A. Cobb Org. Biomo. Chem. 5 2007 3260 3275
4. M. Faria, and H. Ulrich Curr. Opin. Mol. Ther. 10 2008 168 175
5. For selected reviews on conformation restriction of furanose rings, see: E.T. Kool Chem. Rev. 97 1997 1473 1487
6. P. Herdewijn Biochim. Biophys. Acta - Gene Struct. Exp. 1489 1999 167 179
7. C. Simon Nucliosides Mimetics: Their Chemistry and Biological Properties 2001 Gordon and Breaach Science Publishers Amsterdam pp. 3
8. Y. Choi, H.R. Moon, Y. Yoshimura, and V.E. Marquez Nucleosides, Nucleotides and Nucleic Acids 22 2003 547 557
9. M. Petersen, and J. Wengel Trends Biotechnol. 21 2003 74 81
10. L.A. Paquette Aust. J. Chem. 57 2004 7 17
11. For spiroannulation on sugar backbone of nucleosides, see: M. Meldgaard, and J. Wengel J. Chem. Soc. Perkin Trans. 1 2000 3539 3554
12. P. Børsting, A.M. Sørensen, and P. Nielsen Synthesis 2002 797 801
13. L.A. Paquette, C.K. Seekamp, and A.L. Kahane J. Org. Chem. 68 2003 8614 8624
14. M.-C. Bonache, C. Chamorro, A. Cordeiro, M.-J. Camarasa, M.-L. Jimeno, and A. San-Félix J. Org. Chem. 69 2004 8758 8766
15. R.E. Hartung, and L.A. Paquette Synthesis 2005 3209 3218
16. S. Sahabuddin, A. Roy, M.G.B. Drew, B.G. Roy, B. Achari, and S.B. Mandal J. Org. Chem. 71 2006 5980 5992
17. A. Roy, B. Achari, and S.B. Mandal Tetrahedron Lett. 47 2006 3875 3879
18. S. Tripathi, B.G. Roy, M.G.B. Drew, B. Achari, and S.B. Mandal J. Org. Chem. 72 2007 7427 7430
19. K.W. Choi, and M.A. Brimble Org. Biomol. Chem. 7 2009 1424 1436
20. K. Versteeg, D. Zwilling, H. Wang, and K.M. Church Tetrahedron 66 2010 8145 8150
21. For C(3′)-spiroannulation on nucleoside templates, see: J. Balzarini, M.-J. Pérez-Pérez, A. San-Félix, D. Schols, C.-F. Perno, A.-M. Vandamme, M.-J. Camarasa, and E. De Clercq Proc. Natl. Acad. Sci. 89 1992 4392 4396
22. M.-J. Camarasa, M.-J. Pérez-Pérez, A. San-Félix, J. Balzarini, and E.J. De Clercq Med. Chem. 35 1992 2721 2727
23. H. Jonckheere, J.-M. Taymans, J. Balzarini, S. Velazquez, M.J. Camarasa, J. Desmyter, E. De Clercq, and J. Anne J. Biol. Chem. 269 1994 25255 25258
24. P. Nielsen, K. Larsen, and J. Wengel Acta Chem. Scand. 50 1996 1030 1035
25. S. De Castro, E. Lobatón, M.-J. Pérez-Pérez, A. San-Félix, A. Cordeiro, G. Andrei, R. Snoeck, E. De Clercq, J. Balzarini, M.-J. Camarasa, and S. Velázquez J. Med. Chem. 48 2005 1158 1168
26. A. Arnone, G. Assante, and O.V. de Pava Phytochemistry 29 1990 613 616
27. M. Namikoshi, H. Kobayashi, T. Yoshimoto, and S. Meguro Chem. Lett. 29 2000 308 309
28. H. Mukhopadhyay, H. Mukhopadhyay, T. Yoshimoto, and S. Meguro Tetrahedron 57 2001 9475 9480
29. G. Strobel, E. Ford, J. Worapong, J.K. Harper, A.M. Arif, D.M. Grant, P.C.W. Fung, and R.M.W. Chau Phytochemistry 60 2002 179 183
30. R.E. Ziegert, J. Torang, K. Knepper, and S.J. Brase Comb. Chem. 7 2005 147 169
31. Sato, T.; Ohtake, Nishimoto, M.; Emura, T. K.; Yamaguchi T. M.; Takami K. PCT. Int. Appl. WO2008013277, 2008.
32. For cyclotrimerization on sugar templates, see: F.E. McDonald, H.Y.H. Zhu, and C.R. Holmquist J. Am. Chem. Soc. 117 1995 6605 6606
33. Y. Yamamoto, T. Saigoku, Hisao Nishiyamaa, and Kenji Itohb Chem. Commun. 2004 2702 2703
34. Y. Yamamoto, T. Saigoku, H. Nishiyama, T. Ohgai, and K. Itoh Org. Biomol. Chem. 3 2005 1768 1775
35. P. Novak, R. Pohl, M. Kotora, and M. Hocek Org. Lett. 8 2006 2051 2054
36. Y. Yamamoto, T. Hashimoto, K. Hattori, M. Kikuchi, and H. Nishiyama Org. Lett. 8 2006 3565 3568
37. C.V. Ramana, and S.B. Suryawanshi Tetrahedron Lett. 49 2008 445 448
38. Selected reviews: L.S. Zhou, S. Li, K. Kanno, and T. Takahashi Heterocycles 80 2010 725 738
39. I. Omae App. Organomet. Chem. 22 2008 149 166
40. N. Agenet, O. Buisine, F. Slowinski, V. Gandon, C. Aubert, and M. Malacria Organic Reactions vol. 68 2007 John Wiley and Sons Inc. Hoboken, New Jersey
41. P.R. Chopade, and J. Louie Adv. Synth. Catal. 348 2006 2307 2327
42. Y. Yamamoto Curr. Org. Chem. 9 2005 503 519
43. S. Kotha, E. Brahmachary, and K. Lahiri Eur. J. Org. Chem. 2005 4741 4767
44. For recent total synthesis employing [2+2+2] cyclotrimerization, see: F.E. McDonald, and V. Smolentsev Org. Lett. 4 2002 745 748
45. C. Alayrac, D. Schollmeyer, and B. Witulski Chem. Commun. 2001 1464 1466
46. B. Witulski, A. Zimmermann, and N.D. Gowans Chem. Commun. 8 2002 2984 2985
47. E.A. Anderson, E.J. Alexanian, and E.J. Sorensen Angew. Chem., Int. Ed. 43 2004 1998 2001
48. M. Moser, X. Sun, and T. Hudlicky Org. Lett. 7 2005 5669 5672
49. T. Hudlicky, M. Moser, S.C. Banfield, U. Rinner, J.-C. Chapius, and G.R. Pettit Can. J. Chem. 84 2008 1313 1337
50. C.V. Ramana, S.R. Salian, and R.G. Gonnade Eur. J. Org. Chem. 2007 5483 5486
51. C. Alayrac, D. Schollmeyer, and B. Witulski Chem. Commun. 2009 1464 1466
52. S. Kotha, and P. Khedkar Eur. J. Org. Chem. 2009 730 738
53. C.X. Yuan, C.T. Chang, A. Axelrod, and D. Siegel J. Am. Chem. Soc. 132 2010 5924 5925
54. K.C. Nicolaou, J. Wang, Y. Tang, and L. Botta J. Am. Chem. Soc. 132 2010 11350 11363
55. Y. Zou, and A. Deiters J. Org. Chem. 75 2010 5355 5358
56. D. Dallinger, M. Irfan, A. Suljanovic, and C.O. Kappe J. Org. Chem. 75 2010 5278 5288
57. A.L. McIver, and A. Deiters Org. Lett. 12 2010 1288 1291
58. J. Watanabe, Y. Sugiyama, A. Nomura, S. Azumatei, A. Goswami, N. Saino, and S. Okamoto Macromolecules 43 2010 2213 2218
59. R.A. Bauer, C.M. DiBlasi, and D.S. Tan Org. Lett. 12 2010 2084 2087
60. Y. Komine, and K. Tanaka Org. Lett. 12 2010 1312 1315
61. M. Kobayashi, T. Suda, K. Noguchi, and K. Tanaka Angew. Chem., Int. Ed. 50 2011 1664 1667
62. S.B. Suryawanshi, M.P. Dushing, R.G. Gonnade, and C.V. Ramana Tetrahedron 66 2010 6085 6096
63. R. Mallik, R.G. Gonnade, and C.V. Ramana Tetrahedron 64 2008 219 222
64. C.V. Ramana, R. Mallik, R.G. Gonnade, and M.K. Gurjar Tetrahedron lett. 47 2006 3649 3652
65. H. Hattori, M. Tanaka, M. Fukushima, T. Sasaki, and A. Matsuda J. Med. Chem. 39 1996 5005 5011
66. U. Niedballa, and H. Vorbrüggen J. Org. Chem. 39 1974 3654 3660
67. H. Vorbrüggen, K. Krolikiewicz, and B. Bennua Chem. Ber 114 1981 1234 1255
68. H. Vorbrüggen, and G. Höfle Chem. Ber. 114 1981 1256 1268
69. Y. Ura, Y. Sato, M. Shiotsuki, T. Kondo, and T.-A. Mitsudo J. Mol. Catl. A: Chem. 209 2004 35 39
70. Y. Yamamoto, J.-I. Ishii, H. Nishiyama, and K. Itoh J. Am. Chem. Soc. 126 2004 3712 3713
71. R. Grigg, R. Scott, and P. Stevenson Tetrahedron Lett. 23 1982 2691 2692
72. V. Sridharan, R. Grigg, J. Wang, and J. Xu Tetrahedron 56 2000 8967 8976