Mitsunobu coupling of nucleobases and alcohols: An efficient, practical synthesis for novel nonsugar carbon nucleosides

Journal of Organic Chemistry

Volumn 72, Issue 13, 2007, Pages 5012-5015

  Lu, Weibing ^a   Sengupta, Sujata ^a   Petersen, Jeffrey L ^a   Akhmedov, Novruz G ^a   Shi, Xiaodong ^a  

^a WEST VIRGINIA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON NUCLEOSIDES; DIASTEREOMER;

ALCOHOLS; DERIVATIVES; REGIOSELECTIVITY; SYNTHESIS (CHEMICAL);

AMINES;

ALCOHOL DERIVATIVE; CARBON NUCLEOSIDE; GUANINE DERIVATIVE; NUCLEIC ACID BASE; PEPTIDE NUCLEIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; MITSUNOBU REACTION; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STEREOSPECIFICITY;

ALCOHOLS; CARBON; GUANINE; MOLECULAR STRUCTURE; NUCLEOSIDES;

EID: 34250870683     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070515+     Document Type: Article

References (31)

1. (a) Porcheddu, A.; Giacomelli, G. Curr. Med. Chem. 2005, 12, 2561-2599.
2. (b) Nielsen, P. E. Peptide Nucleic Acids, 2nd ed.; Horizon Bioscience: Norfolk, 2004; pp 207-226.
3. (a) De Clercq, E. Int. J. Antimicrob. Agents 2001, 18, 309-328.
4. (b) Nord, L. D.; Dalley, N. K.; McKernan, A.; Robins, R. K. J. Med. Chem. 1987, 30, 1044-1054.
5. (a) Davis, J. T. Angew. Chem., Int. Ed. 2004, 43, 668-698.
6. (b) Ma, L.; Iezzi, M. A.; Kaucher, M. S.; Davis, J. T. J. Am. Chem. Soc. 2006, 128, 15269-15277.
7. (a) Bookser, B. C.; Raffaele, N. B. J. Org. Chem. 2007, 72, 173-179.
8. (b) Dolores, V.; Wu, T.; Renders, M.; Laflamme, G.; Herdewijn, P. Tetrahedron 2007, 63, 2634-2646.
9. Barnes, M. J.; Cooper, N.; Davenport, R. J.; Dyke, H. J.; Galleway, F. P.; Galvin, F. C. A.; Gowers, L.; Haughan, A. F.; Lowe, C.; Meissner, J.; Montana, J. G.; Morgan, T.; Picken, C. L.; Watson, R. J. Bioorg. Med. Chem. Lett. 2001, 11, 1081-1083.
10. Hughes, D. L. The Mitsunobu reaction. In Organic Reactions; Oxford: New York, 1992; Vol. 42, pp 335-656.
11. (a) Chen, H.; Li, S. J. Phys. Chem. A 2006, 110, 12360-12362.
12. (b) Robins, M. J.; Zhong, M. J. Org. Chem. 2006, 71, 8901-8906.
13. (c) Garner, P.; Yoo, J. U.; Sarabu, R. Tetrahedron 1992, 48, 4259-4270.
14. Chen, W.; Flavin, M. T.; Filler, R.; Xu, Z. Nucleosides Nucleotides 1996, 15, 1771-1778.
15. Kurti, L.; Czako, B. Strategic Applications of Named Reactions in Organic Synthesis; Elsevier: Boston, MA, 2005; p p294-295.
16. (a) Mitsunobu, O. Synthesis 1981, 1, 1-28.
17. (b) Hughes, D. L. Organic Reactions; Wiley: New York, 1992; Vol. 42, pp 335-656.
18. (a) Kitade, Y.; Ando, T.; Yamaguchi, T.; Hori, A.; Nakanishi, M.; Ueno, Y. Bioorg. Med. Chem. 2006, 14, 5578-5583.
19. (b) Yang, M.; Schneller, S. W.; Korba, B. B. J. Med. Chem. 2005, 48, 5043-5046.
20. (c) Yin, X.; Li, W.; Schneller, S. W. Tetrahedron Lett. 2006, 47, 9187-9189.
21. (a) Yang, M.; Ye, W.; Schneller, S. W. J. Org. Chem. 2004, 69, 3993-3996.
22. (b) Dyatkina, N. B.; Theil, F.; Von Janta-Lipinski, M. Tetrahedron 1995, 51, 761-772.
23. (c) Iyer, M. S.; Palomo, M.; Schilling, K. M.; Xie, Y.; Formanskii, L.; Zembower, D. E. J. Chromatogr., A 2002, 944, 263-267.
24. Besada, P.; Gonzalez-Moa, M. J.; Teran, C.; Santana, L.; Uriarte, E. Synthesis 2002, 16, 2445-2449.
25. (a) Shi, X.; Fettinger, J. C.; Davis, J. T. Angew. Chem., Int. Ed. 2001, 40, 2827-2831.
26. (b) Shi, X.; Mullaugh, K. M.; Fettinger, J. C.; Jiang, Y.; Hofstadler, S. A.; Davis, J. T. J. Am. Chem. Soc. 2003, 125, 10830-10841.
27. When 2d and 1 were reacted at room temperature under diluted conditions, 3d was obtained in less than 10% isolated yield even after running the reaction for 16 h.
28. (a) Zou, R.; Robbins, M. J. Can. J. Chem. 1987, 65, 1436.
29. (b) Choo, H.; Chong, Y.; Chu, C. K. Org. Lett. 2001, 3, 1471-1473.
30. (a) Sznidman, M. L.; Du, J.; Pesyan, A.; Cleory, D. G.; Hurley, K. P.; Waligora, F.; Almond, M. R. Nucleoside, Nucleotides & Nucleic Acids, 2004, 23, 1875-1887.
31. (b) Tiwari, K. N.; Messini, L.; Montgomery, J. A.; Secrist, J. A. Nucleoside, Nucleotides & Nucleic Acids 2001, 20, 743-746.