Synthesis of oxepane ring containing monocyclic, conformationally restricted bicyclic and spirocyclic nucleosides from D-glucose: A cycloaddition approach

Journal of Organic Chemistry

Volumn 72, Issue 19, 2007, Pages 7427-7430

  Tripathi, Subhankar ^a   Roy, Biswajit G ^a   Drew, Michael G B ^b   Achari, Basudeb ^a   Mandal, Sukhendu B ^a  

^a INDIAN INSTITUTE OF CHEMICAL BIOLOGY   (India)

^b UNIVERSITY OF READING   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CONFORMATIONS; CYCLOADDITION; GLUCOSE; HYDROGENOLYSIS; NUCLEOPHILES; SYNTHESIS (CHEMICAL);

INTRAMOLECULAR NITRONES; OXEPANE; REACTION CONDITION; SPIROCYCLIC NUCLEOSIDES;

PARAFFINS;

GLUCOSE; NUCLEOSIDE DERIVATIVE; OXEPANE DERIVATIVE; SPIRO COMPOUND;

AMINOLYSIS; ARTICLE; CONFORMATION; CYCLIZATION; CYCLOADDITION; HYDROGENOLYSIS; REACTION ANALYSIS; SYNTHESIS;

BICYCLO COMPOUNDS, HETEROCYCLIC; GLUCOSE; MOLECULAR CONFORMATION; NUCLEOSIDES; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 34548767051     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070846m     Document Type: Article

References (24)

1. Saenger, W. Principles of Nucleic Acid Structures; Springer: New York, 1984; pp 51-104
2. Altona, C.; Sunderalingam, M. J. Am. Chem. Soc. 1972, 94, 8205-8212.
3. (a) Shin, K. J.; Moon, H. R.; Georgen, C.; Marquez, V. E. J. Org. Chem. 2000, 65, 2172-2178.
4. (b) Russ, P.; Schelling, P.; Scapozza, L.; Folkers, G.; De Clercq, E.; Marquez, V. E. J. Med. Chem. 2003, 46, 5045-5054.
5. (a) Koshkin, A. A.; Nielsen, P.; Meldgaard, M.; Rajwanshi, V. K.; Singh, S. K.; Wengel, J. J. Am. Chem. Soc. 1998, 120, 13252-13253.
6. (b) Rajwanshi, V. K.; Håkansson, A. E.; Sørensen, M. D.; Pitsch, S.; Singh, S. K.; Kumar, R.; Nielsen, P.; Wengel, J. Angew. Chem., Int. Ed. 2000, 39, 1656-1659.
7. (c) Kværnø, L.; Wrightman, R. H.; Wengel, J. J. Org. Chem. 2001, 66, 5106-5112.
8. (a) Hildbrand, S.; Leumann, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1968-1970.
9. (b) Steffens, R.; Leumann, C. J. Am. Chem. Soc. 1999, 121, 3249-3255.
10. Kittaka, A.; Asakura, T.; Kuze, T.; Tanaka, H.; Yamada, N.; Nakamura, K. T.; Miyasaka, T. J. Org. Chem. 1999, 64, 7081-7093 and references cited therein.
11. Ravindra Babu, B.; Keinicke, L.; Petersen, M.; Nielsen, C.; Wengel, J. Org. Biomol. Chem. 2003, 1, 3514-3526.
12. Nielsen, P.; Larsen, K.; Wengel, J. Acta Chem. Scand. 1996, 50, 1030-1035.
13. (a) Dong, S.; Paquette, L. A. J. Org. Chem. 2005, 70, 1580-1596.
14. (b) Horning, R.; Paquette, L. A. J. Org. Chem. 2005, 70, 1597-1604.
15. (c) Paquette, L. A.; Dong, S. J. Org. Chem. 2005, 70, 5655-5664.
16. (d) Paquette, L. A. Aust. J. Chem. 2004, 57, 7-17 and references cited therein.
17. (a) Roy, A.; Achari, B.; Mandal, S. B. Tetrahedron Lett. 2006, 47, 3875-3879.
18. (b) Sahabuddin, Sk.; Roy, A.; Drew, M, G. B.; Roy, B. G.; Achari, B.; Mandal, S. B. J. Org. Chem. 2006, 71, 5980-5992.
19. Mandal, S. B.; Sahabuddin, Sk.; Singha, K.; Roy, A.; Roy, B. G.; Maity, J. K.; Achari, B. Proc Indian Natl. Sci. Acad., Part A 2005, 71, 283-307.
20. Bhattacharjee, A.; Dutta, S.; Chattopadhyay, P.; Ghoshal, N.; Kundu, A. P.; Pal, A.; Mukhopadhyay, R.; Chowdhury, S.; Bhattacharjya, A.; Patra, A. Tetrahedron 2003, 59, 4623-4639.
21. Vorbrüggen, H.; Krolikiewicz, K.; Bennua, B. Chem. Ber. 1981, 114, 1234-1255.
22. ORTEP diagrams are given in the Supporting Information.
23. Tripathi, S.; Maity, J. K.; Achari, B.; Mandal, S. B. Carbohydr. Res. 2005, 360, 1081-1087.
24. Youssefyeh, R. D.; Verheyden, J. P. H.; Moffatt, J. G. J. Org. Chem. 1979, 44, 1301-1309.