The isochroman- and 1,3-dihydroisobenzofuran-annulation on carbohydrate templates via [2+2+2]-cyclotrimerization and synthesis of some tricyclic nucleosides

Tetrahedron

Volumn 66, Issue 32, 2010, Pages 6085-6096

  Suryawanshi, Sharad B ^a   Dushing, Mangesh P ^a   Gonnade, Rajesh G ^a   Ramana, C V ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

2+2+2 Cyclotrimerization; Dihydroisobenzofuran; Dihydroisobenzopyran; Modified nucleosides; Vorbr ggen reaction

Indexed keywords

ALKYNE; BENZOFURAN DERIVATIVE; CARBOHYDRATE; FUNCTIONAL GROUP; ISOCHROMAN DERIVATIVE; NUCLEOSIDE ANALOG; PYRIMIDINE;

ALKYNYLATION; ANNULATION REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLOTRIMERIZATION; DEACETYLATION; ENANTIOMER; GLYCOSIDATION; MASS SPECTROMETRY; NUCLEAR OVERHAUSER EFFECT; POLYMERIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 77955426007     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.06.011     Document Type: Article

References (97)

1. L.O. Haustedt, C. Mang, K. Siems, and H. Schiewe Curr. Opin. Drug Discovery Dev 9 2006 445 462
2. D.E.G. Shuker Annu. Rep. Prog. Chem., Sect. B 9 2007 165 173
3. D.J. Triggle Biochem. Pharmacol. 78 2009 217 223
4. L.A. Wessjohann, and E. Ruijter Top. Curr. Chem. 243 2005 137 184
5. T.E. Nielsen, and S.L. Schreiber Angew. Chem., Int. Ed. 47 2008 48 56
6. S.L. Schreiber Nature 457 2009 153 154
7. K. Hübel, T. Lehmann, and H. Waldmann Chem. Soc. Rev. 37 2008 1361 1374
8. K. Kumar, and H. Waldmann Angew. Chem., Int. Ed. 48 2009 3224 3242
9. R.M. Wilson, and S.J. Danishefsky J. Org. Chem. 71 2006 8329 8351
10. R.M. Wilson, and S.J. Danishefsky J. Org. Chem. 72 2007 4293 4305
11. J.W. Herndon Coord. Chem. Rev. 253 2009 86 179
12. M. Peuchmaur, and Y.S. Wong Comb. Chem. High Throughput Screening 11 2008 587 601
13. C.V. Ramana, S.B. Suryawanshi, and R.G. Gonnade J. Org. Chem. 74 2009 2842 2845
14. C.V. Ramana, R. Mallik, and G. Sahoo Tetrahedron Lett. 50 2009 4844 4847
15. C.V. Ramana, B. Induvadana, B. Srinivas, K. Yadagiri, M.N. Deshmukh, and R.G. Gonnade Tetrahedron 65 2009 9819 9832
16. C.V. Ramana, and B. Induvadana Tetrahedron Lett. 50 2009 271 273
17. C.V. Ramana, R. Mallik, and R.G. Gonnade Tetrahedron 64 2008 219 233
18. W. Reppe, and W.J. Sweckendiek Justus Liebigs Ann. Chem. 560 1948 104 116
19. K.P.C. Vollhardt Angew. Chem., Int. Ed. Engl. 23 1984 539 556
20. C.V. Ramana, and S.B. Suryawanshi Tetrahedron Lett. 49 2008 445 448
21. F.E. McDonald, H.Y.H. Zhu, and C.R. Holmquist J. Am. Chem. Soc. 117 1995 6605 6606
22. Y. Yamamoto, T. Saigoku, T. Ohgai, H. Nishiyamaa, and K. Itohb Chem. Commun. 2004 2702 2703
23. Y. Yamamoto, T. Hashimoto, K. Hattori, M. Kikuchi, and H. Nishiyama Org. Lett. 8 2006 3565 3568
24. P. Novak, R. Pohl, M. Kotora, and M. Hocek Org. Lett. 8 2006 2051 2054
25. For reports dealing with the cyclotrimerization of sugar alkynes see: R. Roy, S.K. Das, R. Dominique, C.M. Trono, F. Hernndez-Mateo, and F. Santoyo-Gonzlez Pure Appl. Chem. 71 1999 565 571
26. R. Dominique, B. Liu, S.K. Das, and R. Roy Synthesis 2000 862 868
27. For selected reviews see: K. Tanaka Chem. - Asian J. 4 2009 508 518
28. T. Shibata, and K. Tsuchikama Org. Biomol. Chem. 2008 1317 1323
29. N. Agenet, O. Buisine, F. Slowinski, V. Gandon, C. Aubert, and M. Malacria T.V. RajanBabu, Organic Reactions Vol. 68 2007 John Wiley Hoboken 1 302
30. V. Gandon, C. Aubert, and M. Malacria Chem. Commun. 2006 2209 2217
31. S. Kotha, E. Brahmachary, and K. Lahiri Eur. J. Org. Chem. 2005 4741 4767
32. V. Gandon, C. Aubert, and M. Malacria Curr. Org. Chem. 9 2005 1699 1712
33. Y. Yamamoto Curr. Org. Chem. 9 2005 503 519
34. M. Rubin, A.W. Sromek, and V. Gevorgyan Synlett 2003 2265 2291
35. C. Aubert, O. Buisine, M. Petit, F. Slowinski, and M. Malacria Pure Appl. Chem. 71 1999 1463 1470
36. N.E. Schore B.M. Trost, I. Fleming, L.A. Paquette, Comprehensive Organic Synthesis Vol. 5 1991 Pergamon Oxford 1129
37. For recent total synthesis employing [2+ 2+2] cycloadditions see: F.E. McDonald, and V. Smolentsev Org. Lett. 4 2002 745 748
38. C. Alayrac, D. Schollmeyer, and B. Witulski Chem. Commun. 2002 1464 1466
39. B. Witulski, A. Zimmermann, and N.D. Gowans Chem. Commun. 2002 2984 2985
40. E.A. Anderson, E.J. Alexanian, and E.J. Sorensen Angew. Chem., Int. Ed. 43 2004 1998 2001
41. M. Moser, X. Sun, and T. Hudlicky Org. Lett. 7 2005 5669 5672
42. T. Hudlicky, M. Moser, S.C. Banfield, U. Rinner, J.-C. Chapius, and G.R. Pettit Can. J. Chem. 84 2006 1313 1337
43. C.V. Ramana, S.R. Salian, and R.G. Gonnade Eur. J. Org. Chem. 2007 5483 5486
44. C. Alayrac, D. Schollmeyer, and B. Witulski Chem. Commun. 2009 1464 1466
45. E.L. Larghi, and T.S. Kaufman Synthesis 2006 187 220
46. S. Arimitsu, and G.B. Hammond J. Org. Chem. 71 2006 8665 8668
47. R. Rodrigo Tetrahedron 44 1988 2093 2135
48. E.A. Markaryan, and A.G. Samodurova Russ. Chem. Rev. 58 1989 479 493
49. P.J. Curtis, and J.F. Grove Nature 160 1947 574 575
50. J.F. Grove, and P.B. Hitchcock J. Chem. Soc., Perkin Trans. 1 1986 1145 1146
51. D. Parisot, D.M. Devys, J.P. Ferezou, and M. Barbier Phytochemistry 22 1983 1301 1303
52. W. Pushan, G. Xuanliang, W. Yixiong, Y. Fukuyama, I. Miura, and M. Sugawara Phytochemistry 23 1984 2033 2038
53. J.M. McCall, R.B. McCall, R.E. TenBrink, B.V. Kamdar, S.J. Humphrey, V.H. Sethy, D.W. Harris, and C. Daenzer J. Med. Chem. 25 1982 75 81
54. R.E. TenBrink, C.L. Bergh, J.N. Duncan, D.W. Harris, R.M. Huff, R.A. Lahti, C.F. Lawson, B.S. Lutzke, I.J. Martin, S.A. Rees, S.K. Schlachter, J.C. Sih, and M.W. Smith J. Med. Chem. 39 1996 2435 2437
55. B. Unterhalt, R. Jöstingmeier, and A. Sanatgar Pharmazie 52 1997 186 189
56. P.S. Bury, L.B. Christiansen, P. Jacobsen, A.S. Jorgensen, A. Kanstrup, L. Narum, S. Bain, C. Fledelius, B. Gissel, B.S. Hansen, N. Korsgaard, S.M. Thorpe, and K. Wassermann Bioorg. Med. Chem. 10 2002 125 145
57. J. Liu, E.T. Birzin, W. Chan, Y.T. Yang, L.-Y. Pai, C. DaSilva, E.C. Hayes, R.T. Mosley, F. DiNinno, S.P. Rohrer, J.M. Schaeffer, and M.L. Hammond Bioorg. Med. Chem. Lett. 15 2005 715 718
58. T. Suzuki, K. Tanemura, T. Horaguchi, and K. Kaneko Tetrahedron 62 2006 3739 3751
59. P. Mohr, M. Decker, C. Enzensperger, and J. Lehmann J. Med. Chem. 49 2006 2110 2116
60. For aromatic ring annulation on sugar templates see: O.R. Martin Carbohydr. Res. 171 1987 211 222
61. O.R. Martin, C.A.V. Hendricks, P.P. Deshpande, B. Amos, A.B. Cutler, S.A. Kane, and S.P. Rao Carbohydr. Res. 196 1990 41 58
62. S.S. Kulkarni, Y.-H. Liu, and S.-C. Hung J. Org. Chem. 70 2005 2808 2811
63. K.P. Kaliappan, and V. Ravikumar Org. Biomol. Chem. 3 2005 848 851
64. S. Hotha, and S.K. Maurya Tetrahedron Lett. 47 2006 3307 3310
65. M. Adharvana, and K.S. Chari Synthesis 2005 708 710
66. S. Ohira Synth. Commun. 19 1989 561 564
67. G.J. Roth, B. Liepold, S.G. Müller, and H.J. Bestmann Synlett 1996 521 522
68. K.H. Dötz, D. Paetsch, and H.L. Bozec J. Organomet. Chem. 589 1999 11 20
69. P.C.M. Herve Du Penhoat, and A.S. Perlin Carbohydr. Res. 71 1979 135 148
70. For a review of the rhodium-catalyzed [2+2+2]-cycloadditions, see M. Fujiwara, and I. Ojima P.A. Evans, Modern Rhodium-Catalyzed Organic Reactions 2005 Wiley-VCH Weinheim 129 Chapter 7
71. M. Shanmugasundaram, M.-S. Wu, and C.-H. Cheng Org. Lett. 3 2001 4233 4236
72. Y. Yamamoto, J.-I. Ishii, H. Nishiyama, and K. Itoh J. Am. Chem. Soc. 126 2004 3712 3713
73. Y. Yamamoto, J.-I. Ishii, H. Nishiyama, and K. Itoh J. Am. Chem. Soc. 127 2005 9625 9631
74. For selected reviews on sugar modification in nucleosides, see: C. Wilson, and A.D. Keefe Curr. Opin. Chem. Biol. 10 2006 607 614
75. D.R. Corey J. Clin. Invest. 117 2007 3615 3622
76. A.J.A. Cobb Org. Biomol. Chem. 5 2007 3260 3275
77. M. Faria, and H. Ulrich Curr. Opin. Mol. Ther. 10 2008 168 175
78. For selected reviews on conformation restriction of furanose rings, see: E.T. Kool Chem. Rev. 97 1997 1473 1488
79. P. Herdewijn Biochim. Biophys. Acta, Gene Struct. Expression 1489 1999 167 179
80. C. Simon Nucleosides Mimetics: Their Chemistry and Biological Properties 2001 Gordon and Breach Science Amsterdam p 3
81. Y. Choi, H.R. Moon, Y. Yoshimura, and V.E. Marquez Nucleosides, Nucleotides Nucleic Acids 22 2003 547 557
82. M. Petersen, and J. Wengel Trends Biotechnol. 21 2003 74 81
83. L.A. Paquette Aust. J. Chem. 57 2004 7 17
84. 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. U.S.A 89 1992 4392 4396
85. M.-J. Camarasa, M.-J. Pérez Pérez, A. San-Félix, J. Balzarini, and E. De Clercq J. Med. Chem. 35 1992 2721 2727
86. 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
87. P. Nielsen, K. Larsen, and J. Wengel Acta Chem. Scand. 50 1996 1030 1035
88. 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
89. U. Niedballa, and H. Vorbrüggen J. Org. Chem. 39 1974 3654 3660
90. H. Vorbrüggen, K. Krolikewiez, and B. Bennua Chem. Ber. 114 1981 1234 1255
91. H. Vorbrüggen, and G. Höfle Chem. Ber. 114 1981 1256 1268
92. 2. Hydrogen atoms were included in the refinement as per the riding model
93. G.M. Sheldrick SHELX-97 Program for Crystal Structure Solution and Refinement 1997 University of Gottingen Germany
94. The crystallographic data has been deposited with the Cambridge Crystallographic Data Centre as deposition No. CCDC768342 (33) CCDC768343 (37) and CCDC768344 (40). Copies of the data can be obtained, free of charge, on application to the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 1223 336033; e-mail: deposit@ccdc.cam.ac.uk ].
95. P.L. Durette, and D. Horton J. Org. Chem. 36 1971 2658 2669
96. K.A. Durugkar, C.V. Ramana, V.G. Puranik, S.B. Narute, and B.L.V. Prasad Tetrahedron Lett. 49 2008 6227 6230
97. B. Bernet, and A. Vasella Helv. Chim. Acta 83 2000 995 1021