Exploitation of in situ generated sugar-based olefin Keto-Nitrones: Synthesis of carbocycles, heterocycles, and nucleoside derivatives

Journal of Organic Chemistry

Volumn 80, Issue 2, 2015, Pages 1136-1148

  Das, Soumendra Nath ^a   Chowdhury, Arpan ^b   Tripathi, Neha ^b   Jana, Prithwish K ^a   Mandal, Sukhendu B ^a  

^a INDIAN INSTITUTE OF CHEMICAL BIOLOGY   (India)

^b NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BIOMOLECULES; CRYSTAL STRUCTURE; CYCLOADDITION; OLEFINS; SINGLE CRYSTALS; X RAY ANALYSIS;

CYCLOADDITION PRODUCTS; CYCLOADDITION REACTION; CYCLOHEPTANES; KETO-NITRONES; NUCLEOSIDE DERIVATIVES; REACTION CONDITIONS; SINGLE CRYSTAL X-RAY ANALYSIS; TETRA-HYDROFURAN;

SYNTHESIS (CHEMICAL);

ACETALDEHYDE; ALKENE DERIVATIVE; AMINOALCOHOL; CARBOHYDRATE DERIVATIVE; CYCLOHEPTANE DERIVATIVE; CYCLOPENTANE DERIVATIVE; HETEROCYCLIC COMPOUND; ISOXAZOLIDINE DERIVATIVE; KETONE DERIVATIVE; NITROGEN; NITRONE DERIVATIVE; NUCLEOSIDE ANALOG; NUCLEOSIDE DERIVATIVE; OXEPANE DERIVATIVE; OXYGEN; SODIUM BOROHYDRIDE; SODIUM HYDROXIDE; SULFUR; TETRABUTYLAMMONIUM; TETRAHYDROFURAN DERIVATIVE; ALKENE; CARBOHYDRATE; FURAN DERIVATIVE; FUSED HETEROCYCLIC RINGS; NITROGEN OXIDE; NITRONES; NUCLEOSIDE; TETRAHYDROFURAN;

ACETYLATION; ALLYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CYCLIZATION; CYCLOADDITION; GLYCOSIDATION; HYDROGENATION; HYDROGENOLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; STAUDINGER REACTION; STEREOCHEMISTRY; STEREOSPECIFICITY; SWERN OXIDATION; SYNTHESIS; X RAY ANALYSIS; CHEMISTRY; STEREOISOMERISM; X RAY CRYSTALLOGRAPHY;

ALKENES; BICYCLO COMPOUNDS, HETEROCYCLIC; CARBOHYDRATES; CRYSTALLOGRAPHY, X-RAY; CYCLOADDITION REACTION; FURANS; NITROGEN OXIDES; NUCLEOSIDES; STEREOISOMERISM;

EID: 84921417206     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo502672x     Document Type: Article

References (94)

1. Jones, R. C. F. and Martin, J. N. In Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products; Padwa, A. and Pearson, W. H., Eds.; John Wiley & Sons, Inc: New York, 2002; Chapter 1, pp 1-81.
2. Merino, P. Nitrones and its Cyclic Analogues. In Science of Synthesis; Bellus, D. and Padwa, A., Eds.; George Thieme: Stuttgart, Germany, 2004; Vol. 27, pp 511-580.
3. Merino, P. Nitrones and Cyclic Analogues. An Update. In Science of Synthesis; Schaumann, E., Ed.; George Thieme: Stuttgart, Germany, 2011; Vol. 2010/4, pp 325-403.
4. Baggiolini, E. G.; Lee, H. L.; Pizzolato, G.; Uskokovic, M. R. J. Am. Chem. Soc. 1982, 104, 6460-6462
5. Tufariello, J. J.; Meckler, H.; Senaratne, K. P. A. Tetrahedron 1985, 41, 3447-3453
6. Wovkulich, P. M.; Uskokovic, M. R. J. Am. Chem. Soc. 1981, 103, 3956-3958
7. Wovkulich, P. M.; Uskokovic, M. R. Tetrahedron 1985, 41, 3455-3462
8. Funk, R. L.; Bolton, G. L.; Daggett, J. U.; Hansen, M. M.; Horcher, L. H. M. Tetrahedron 1985, 41, 3479-3495
9. Iida, H.; Kasahara, K.; Kibayashi, C. J. Am. Chem. Soc. 1986, 108, 4687-4648
10. Kong, K.; Enquist, J. A., Jr.; McCallum, M. E.; Smith, G. M.; Matsumaru, T.; Menhaji-Klotz, E.; Wood, J. L. J. Am. Chem. Soc. 2013, 135, 10890-10893
11. Yang, D.; Micalizio, G. C. J. Am. Chem. Soc. 2012, 134, 15237-15240
12. Krenske, E. H.; Agopcan, S.; Aviyente, V.; Houk, K. N.; Johnson, B. A.; Holmes, A. B. J. Am. Chem. Soc. 2012, 134, 12010-12015
13. Davis, F. A.; Gaddiraju, N. V.; Theddu, N.; Hummel, J. R.; Kondaveeti, S. K.; Zdilla, M. J. J. Org. Chem. 2012, 77, 2345-2359
14. Zhang, X.; Cividino, P.; Poisson, J.-F.; Shpak-Kraievskyi, P.; Lawent, M. Y.; Martel, A.; Dujardin, G.; Py, S. Org. Lett. 2014, 16, 1936-1939
15. Nguyen, T. B.; Beauseigneur, A.; Martel, A.; Dhal, R.; Laurent, M.; Dujardin, G. J. Org. Chem. 2010, 75, 611-620
16. Ernst, B.; Hart, G. W.; Sinaÿ, P., Eds. Carbohydrates in Chemistry and Biology; Wiley-VCH: Weiheim, Germany, 2000; Vol. 1.
17. Tamura, O.; Mita, N.; Kusaka, N.; Suzuki, H.; Sakamoto, M. Tetrahedron Lett. 1997, 38, 429-432
18. Faltin, F.; Fehring, V.; Kadyrov, R.; Arrieta, A.; Schareina, T.; Selke, R.; Miethchen, R. Synthesis 2001, 638-646
19. Totani, K.; Takao, K.; Tadano, K. Synlett 2004, 2066-2080
20. Shing, T. K. M.; Elsley, D. A.; Gillhouley, J. G. J. Chem. Soc., Chem. Commun. 1989, 1280-1282
21. Ferrier, R. J.; Furneaux, R. H.; Prasit, P.; Tylor, P. C.; Brown, K. L.; Gainsford, G. J.; Diehl, J. W. J. Chem. Soc., Perkin Trans I 1983, 1621-1628
22. Majumder, S.; Bhattacharjya, A.; Patra, A. Tetrahedron Lett. 1997, 38, 8581-8584
23. Koumbis, A. E.; Gallos, J. K. Curr. Org. Chem. 2003, 7, 585-628
24. Fišera, L. In Heterocycles from Carbohydrate Precursors; Sayed, E.; Ashry, H. E., Eds.; Springer-Verlag: Berlin, 2007; Chapter 8, pp 287-323.
25. Patra, R.; Bar, N. C.; Roy, A.; Achari, B.; Ghoshal, N.; Mandal, S. B. Tetrahedron 1996, 52, 11265-11272
26. Chakraborty, C.; Vyavahare, V. P.; Dhavale, D. D. Tetrahedron 2007, 63, 11984-11990
27. Sahabuddin, Sk.; Roy, A.; Drew, M. G. B.; Roy, B. G.; Achari, B.; Mandal, S. B. J. Org. Chem. 2006, 71, 5980-5992
28. Singha, K.; Roy, A.; Dutta, P. K.; Tripathy, S.; Sahabuddin, Sk.; Achari, B.; Mandal, S. B. J. Org. Chem. 2004, 69, 6507-6011
29. Roy, A.; Achari, B.; Mandal, S. B. Tetrahedron Lett. 2006, 47, 3875-3879
30. Bhattacharjya, A.; Chattopadhyay, P.; McPhail, A. T.; McPhail, D. R. J. Chem. Soc., Chem. Commun. 1990, 1508-1509
31. 1991, 136. (Corrigendum)
32. Shing, T. K. M.; Zhong, Y.-L.; Mak, T. C. W.; Wang, R.; Xue, F. J. Org. Chem. 1998, 63, 414-415
33. Bhattacharjee, A.; Datta, S.; Chattopadhyay, P.; Ghosal, N.; Kundu, A. P.; Pal, A.; Mukhopadhyay, R.; Chowdhury, S.; Bhattacharjya, A.; Patra, A. Tetrahedron 2003, 59, 4623-4639 and references cited therein
34. Brandi, A.; Cardona, F.; Cicchi, S.; Cordero, F. M.; Goti, A. Chem. - Eur. J. 2009, 15, 7808-7821
35. Puchalska, E. M.; Rowicki, T.; Sas, W.; Stawińska, K. M. Tetrahedron 2013, 69, 9826-9831
36. Shing, T. K. M.; Wong, W. F.; Ikeno, T.; Yamada, T. Org. Lett. 2007, 9, 207-209
37. Dondoni, A.; Junquera, F.; Merchán, F. L.; Merino, P.; Scherrmann, M.-C.; Tejero, T. J. Org. Chem. 1997, 62, 5484-5496
38. Dhavale, D. D.; Jachak, S. M.; Karche, N. P.; Trombini, C. Tetrahedron 2004, 60, 3009-3016
39. Li, X.; Takahashi, H.; Ohtake, H.; Ikegami, S. Heterocycles 2003, 59, 547-571
40. Piperno, A.; Giofrè, S. V.; Iannazzo, D.; Romeo, R.; Romeo, G.; Chiacchio, U.; Rescifina, A.; Piotrowska, D. G. J. Org. Chem. 2010, 75, 2798-2805
41. Rong, J.; Roselt, P.; Plavec, J.; Chattopadhyaya, J. Tetrahedron 1994, 50, 4921-4936
42. Mukherjee, S.; Mandal, S. B.; Bhattacharjya, A. RSC Adv. 2012, 2, 8969-8978
43. Ghosh, R.; Maity, J. K.; Achari, B.; Mandal, S. B. J. Org. Chem. 2010, 75, 2419-2422
44. Tripathi, S.; Roy, B. G.; Drew, M. G. B.; Achari, B.; Mandal, S. B. J. Org. Chem. 2007, 72, 7427-7430
45. Bar, N. C.; Roy, A.; Achari, B.; Mandal, S. B. J. Org. Chem. 1997, 62, 8948-8951
46. Siriwardena, A.; Sonawane, D. P.; Bande, O. P.; Markad, P. R.; Yonekawa, S.; Tropak, M. B.; Ghosh, S.; Chopade, B. A.; Mahuran, D. J.; Dhavale, D. D. J. Org. Chem. 2014, 79, 4398-4404 and the references cited therein
47. Liautard, V.; Desvergnes, V.; Martin, O. R. Tetrahedron: Asymmetry 2008, 19, 1999-2002
48. Gao, Z.-X.; Wang, M.; Wang, S.; Yao, Z.-J. Org. Lett. 2009, 11, 3678-3681
49. Farr, R. A.; Peet, N. P.; Fang, N. S. Tetrahedron Lett. 1990, 31, 7109-7112
50. Ferrier, R. J.; Prasit, P. J. Chem. Soc., Chem. Commun. 1981, 983-985
51. Torrente, S.; Noya, B.; Paredes, M. D.; Alonso, R. J. Org. Chem. 1997, 62, 6710-6711
52. Sharma, G. V. M; Reddy, K. R.; Sankar, A. R.; Kunwar, A. C. Tetrahedron Lett. 2001, 42, 8893-8896
53. Shing, T. K. M.; Zhong, Y.-L. Tetrahedron 2001, 57, 1573-1579
54. Collins, P. M.; Ashwood, M. S.; Eder, H.; Wright, S. H. B.; Kennedy, D. J. Tetrahedron Lett. 1990, 31, 2055-2058
55. Bernet, V. B.; Vasella, A. Helv. Chim. Acta 1979, 62, 1990-2016 and references cited therein
56. Silva, A. M. G.; Tomé, A. C.; Neves, M.G. P. M. S.; Silva, A. M. S.; Cavaleiro, J. A. S.; Perrone, D.; Dondoni, A. Tetrahedron Lett. 2002, 43, 603-605
57. Torrente, S.; Noya, B.; Branchadell, V.; Alonso, R. J. Org. Chem. 2003, 68, 4772-4783
58. Osborn, H. M. I.; Gemmel, N.; Harwood, L. M. J. Chem. Soc., Perkin Trans. 1 2002, 22, 2419-2438
59. Tronchet, J. M. J.; Mihaly, M. E. Helv. Chim. Acta 1972, 55, 1266-1271
60. Ma, X.; Tang, Q.; Ke, J.; Zhang, J.; Wang, C.; Wang, H.; Li, Y.; Shao, H. Chem. Commun. 2013, 49, 7085-7087
61. Gowrisankar, S.; Lee, K. Y.; Kim, J. N. Bull. Korean Chem. Soc. 2006, 27, 929-932
62. Sridhar, P. R.; Reddy, G. M.; Seshadri, K. Eur. J. Org. Chem. 2012, 6228-6235
63. Asai, T.; Morita, S.; Shirata, N.; Yaniguchi, T.; Monde, K.; Sakurai, H.; Ozeki, T.; Oshima, Y. Org. Lett. 2002, 14, 5456-5459
64. Harrar, K.; Reiser, O. Chem. Commun. 2012, 48, 3457-3459
65. Weiser, R.; Yue, W.; Reiser, O. Org. Lett. 2005, 7, 5353-5356
66. Wang, G. K.; Lin, B. B.; Rao, R.; Zhu, K.; Quin, X. Y.; Xie, G. Y.; Quin, M. J. Nat. Prod. Res. 2013, 27, 1348-1352
67. Knapp, S.; Gore, V. K. Org. Lett. 2000, 2, 1391-1393
68. Ghosh, A. K.; Chapsal, B. D.; Baldridge, A.; Steffey, M. P.; Walters, D. E.; Koh, Y.; Amano, M.; Mitsuya, H. J. Med. Chem. 2011, 54, 622-634
69. Basu, S.; Ellinger, B.; Rizzo, S.; Deraeve, C.; Schürmann, M.; Preut, H.; Arndt, H.-D.; Waldmann, H. Proc. Natl. Acad. Sci. U.S.A. 2011, 108, 6805-6810
70. Nicolaou, K. C.; Claremon, D. A.; Barnette, W. E. J. Am. Chem. Soc. 1980, 102, 6611-6612
71. Debus, O. M.; Kurlmann, G. Epilepsia 2004, 45, 103-108
72. Sall, K. N.; Greff, L. J.; Johnson-Pratt, L. R.; Delucca, P. T.; Polis, A. B.; Kolodny, A. H.; Fletcher, C. A.; Cassel, D. A.; Boyle, D. R.; Skobieranda, F. Opthalmology 2003, 110, 615-624
73. Ilardi, E. A.; Vitaku, E.; Njardarson, J. T. J. Med. Chem. 2014, 57, 2832-2842
74. Castanheiro, T.; Donnard, M.; Gulea, M.; Suffert, J. Org. Lett. 2014, 16, 3060-3063
75. McReynolds, M. D.; Dougherty, J. M.; Hanson, P. R. Chem. Rev. 2004, 104, 2239-2258 and references cited therein
76. Oppolzer, W. Pure Appl. Chem. 1990, 62, 1241-1250
77. Norbeck, D. W.; Spanton, S.; Broder, S.; Mitsuya, H. Tetrahedron Lett. 1989, 30, 6263-6266
78. Chu, C. K.; Beach, J. W.; Jeong, L. S.; Choi, B. G.; Comer, F. I.; Alves, A. J.; Schinazi, R. F. J. Org. Chem. 1991, 56, 6503-6505
79. Merino, P. In Chemical Synthesis of Nucleoside Analogues; Wiley: Hoboken, NJ, 2013.
80. Yadav, J. S.; Reddy, B. V. S. Carbohydr. Res. 2000, 329, 885-888
81. Oikawa, Y.; Yoshioka, T.; Yonemitsu, O. Tetrahedron Lett. 1982, 23, 885-888
82. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277-7287
83. Garegg, P. J.; Samuelsson, B. J. Chem. Soc., Perkin Trans. 1 1980, 2866-2869
84. Omura, K.; Sharma, A. K.; Swern, D. J. Org. Chem. 1976, 41, 957-962
85. Staudinger, H.; Meyer, J. Helv. Chim. Acta 1919, 2, 635-646
86. Jones, J. K. N.; Thompson, J. L. Can. J. Chem. 1957, 35, 955-959
87. Paquette, L. A.; Zeng, Q.; Tusi, H.-C.; Johnston, J. N. J. Org. Chem. 1998, 63, 8491-8509
88. Dam, J. H.; Fristrup, P.; Madsen, R. J. Org. Chem. 2008, 73, 3228-3235
89. Wolfrom, M. L.; Hanessian, S. J. Org. Chem. 1962, 27, 1800-1804
90. Yoshimura, Y.; Kitano, K.; Satoh, H.; Watanabe, M.; Miura, S.; Sakata, S.; Sasaki, T.; Matsuda, A. J. Org. Chem. 1996, 61, 822-823
91. Mukherjee, S.; Roy, B. G.; Das, S. N.; Mandal, S. B. Tetrahedron Lett. 2012, 53, 4929-4932
92. Cicchi, S.; Goti, A.; Brandi, A.; Guarna, A.; De Sarlo, F. Tetrahedron Lett. 1990, 31, 3351-3354
93. Vorbrüggen, H.; Höfle, G. Chem. Ber. 1981, 114, 1256-1268
94. Wang, Z. In Comprehensive Organic Name Reactions and Reagents; Wiley: Hoboken, NJ, 2010.