A general and enantioselective approach to pentoses: A rapid synthesis of PSI-6130, the nucleoside core of sofosbuvir

Journal of the American Chemical Society

Volumn 136, Issue 16, 2014, Pages 5900-5903

  Peifer, Manuel ^a   Berger, Raphaëlle ^a   Shurtleff, Valerie W ^a   Conrad, Jay C ^a   Macmillan, David W C ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOSELECTIVITY; KETONES;

C-NUCLEOSIDES; ENANTIOSELECTIVE; ENANTIOSELECTIVE APPROACH; MUKAIYAMA ALDOLS; OXIDATION REACTIONS; PHARMACEUTICALLY ACTIVE COMPOUNDS; RAPID SYNTHESIS; SYNTHETIC STRATEGIES;

BIOMOLECULES;

2' DEOXY 2' FLUORO 2' METHYLCYTIDINE; CUPRIC ION; LACTONE; NUCLEOSIDE; PENTOSE; SOFOSBUVIR; 2'-DEOXY-2'-FLUORO-2'-C-METHYLCYTIDINE; DEOXYCYTIDINE; URIDINE PHOSPHATE;

ARTICLE; CATALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; MUKAIYAMA REACTION; OXIDATION REDUCTION REACTION; ANALOGS AND DERIVATIVES; CHEMISTRY; ENZYME SPECIFICITY; KINETICS; STEREOISOMERISM; SYNTHESIS;

CHEMISTRY TECHNIQUES, SYNTHETIC; DEOXYCYTIDINE; KINETICS; PENTOSES; SOFOSBUVIR; STEREOISOMERISM; SUBSTRATE SPECIFICITY; URIDINE MONOPHOSPHATE;

EID: 84899536192     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja502205q     Document Type: Article

References (24)

1. Nelson, D. L.; Cox, M. M. Lehninger Principles of Biochemistry, 5 th ed.; W. H. Freeman and Co.: New York, 2008; pp 271-299.
2. Sofia, M. J.; Bao, D.; Chang, W.; Du, J.; Nagarathnam, D.; Rachakanda, S.; Reddy, P. G.; Ross, B. S.; Wang, P.; Zhang, H. R.; Bansal, S.; Espiritu, C.; Keilman, M.; Lam, A. M.; Micolochick Steuer, H. M.; Niu, C.; Otto, M. J.; Furman, P. A. J. Med. Chem. 2010, 53, 7202
3. Clark, J. L.; Hollecker, L.; Mason, J. C.; Stuyver, L. J.; Tharnish, P. M.; Lostia, S.; McBrayer, T. R.; Schinazi, R. F.; Watanabe, K. A.; Otto, M. J.; Furman, P. A.; Stec, W. J.; Patterson, S. E.; Pankiewicz, K. W. J. Med. Chem. 2005, 48, 5504
4. For a general review of the de novo synthesis of monosaccharides: Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195
5. For a review of the synthesis of carbohydrates from acyclic precursors: Ager, D. J.; East, M. B. Tetrahedron 1993, 49, 5683
6. For a review of the asymmetric de novo synthesis of monosaccharides: Vogel, P.; Robina, I. De Novo Synthesis of Monosaccharides. In Glycoscience; Fraser-Reid, B.; Tatsuka, K.; Thiem, J., Eds.; Springer-Verlag: Berlin, 2008, pp 857-956.
7. Trost, B. M.; Nübling, C. Carbohydr. Res. 1990, 202, 1
8. Northrup, A. B.; MacMillan, D. W. C. Science 2004, 305, 1752
9. Bär, E.; Fischer, H. O. L. J. Am. Chem. Soc. 1939, 61, 761
10. Debost, J. L.; Gelas, J.; Horton, D. J. Org. Chem. 1983, 48, 1381
11. Hertel, L. W.; Kroin, J. S.; Misner, J. W.; Tustin, J. M. J. Org. Chem. 1988, 53, 2406
12. Zhang, P. S.; Idling, H.; Cedilote, M.; Brunner, S.; Williamson, T.; Cleary, T. P. Tetrahedron: Asymmetry 2009, 20, 305
13. Simonovich, S. P.; Van Humbeck, J. F.; MacMillan, D. W. C. Chem. Sci. 2012, 3, 58
14. Van Humbeck, J. F.; Simonovich, S. P.; Knowles, R. R.; MacMillan, D. W. C. J. Am. Chem. Soc. 2010, 132, 10012
15. Murakami, M.; Matsuo, J. Angew. Chem., Int. Ed. 2013, 52, 9109
16. Kita, Y.; Tamura, O.; Itoh, F.; Yasuda, H.; Kishino, H.; Ke, Y. Y.; Tamura, Y. J. Org. Chem. 1988, 53, 554
17. Terada, M.; Gu, J.-H.; Deka, D. C.; Mikami, K.; Nakai, T. Chem. Lett. 1992, 21, 29
18. For a review of the synthesis and biological applications of C -nucleosides: Stambasky, J.; Hocek, M.; Kocovsky, P. Chem. Rev. 2009, 109, 6729
19. For a general review of the synthesis of C-glycosides: Du, Y.; Linhardt, R. J. Tetrahedron 1998, 54, 9913
20. Metobo, S. E.; Xu, J.; Saunders, O. L.; Butler, T.; Aktoudianakis, E.; Cho, A.; Kim, C. U. Tetrahedron Lett. 2012, 53, 484
21. Review of the synthesis of fluorinated nucleosides: Liu, P.; Sharon, A.; Chu, C. K. J. Fluorine Chem. 2008, 129, 743
22. Chou, T. S.; Heath, P. C.; Patterson, L. E.; Poteet, L. M.; Lakin, R. E.; Hunt, A. H. Synthesis 1992, 565
23. Chang, Y. K.; Lee, J.; Park, G.-S.; Lee, M.; Park, C. H.; Kim, H. K.; Lee, G.; Lee, B.-Y.; Baek, J. Y.; Kim, K. S. Tetrahedron 2010, 66, 5687
24. Wang, P.; Chun, B.-K.; Rachakonda, S.; Du, J.; Zhan, N.; Shi, J.; Stec, W.; Cleary, D.; Ross, B. S.; Sofia, M. J. J. Org. Chem. 2009, 74, 6819