High 1,3-trans stereoselectivity in nucleophilic substitution at the anomeric position and β-fragmentation of the primary alkoxyl radical in 3-amino-3-deoxy-ribofuranose derivatives: Application to the synthesis of 2- epi -(-)-jaspine B

Journal of Organic Chemistry

Volumn 76, Issue 13, 2011, Pages 5466-5471

  Sánchez Eleuterio, Alma ^a   Quintero, Leticia ^a   Sartillo Piscil, Fernando ^a  

^a BENEMÉRITA UNIVERSIDAD AUTÓNOMA DE PUEBLA   (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

ALKOXYL RADICALS; ANOMERIC POSITION; BENZYLAMINES; FIVE-MEMBERED RINGS; NUCLEOPHILIC ATTACK; NUCLEOPHILIC SUBSTITUTIONS; OXOCARBENIUM; TOTAL SYNTHESIS;

STEREOSELECTIVITY;

2 EPI JASPINE B; 3 AMINO 3 DEOXYRIBOFURANOSE DERIVATIVE; AMINO ACID DERIVATIVE; BENZYLAMINE DERIVATIVE; NUCLEOPHILE; OXOCARBENIUM ION; PHTHALIMIDE DERIVATIVE; RADICAL; UNCLASSIFIED DRUG;

AMINO ACID SUBSTITUTION; ARTICLE; CHEMICAL REACTION; FRAGMENTATION REACTION; NUCLEOPHILICITY; STEREOCHEMISTRY;

ALCOHOLS; AMINO SUGARS; MOLECULAR CONFORMATION; SPHINGOSINE; STEREOISOMERISM;

EID: 79959678786     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo200639t     Document Type: Article

References (45)

1. Postema, M. H. D. C-Glycoside Synthesis; CRS Press: Boca Raton, 1995.
2. Levy, D. E.; Tang, C. In The Chemistry of C-Glycosides; Pergamon: Oxford, 1995.
3. Suzuki, K.; Matsumoto, T. Synthesis of Glycosylarenes. In Preparative Carbohydrate Chemistry; Hanessian, S., Ed.; Marcel Dekker: New York, 1997.
4. Harmange, J.-L.; Figaderé, B. Tetrahedron: Asymmetry 1993, 4, 1711
5. Du, Y.; Linhardt, R. J. Tetrahedron 1998, 54, 9913
6. Yasumoto, T.; Muratat, M. Chem. Rev. 1993, 93, 1897
7. Wong, H. N. C. Eur. J. Org. Chem. 1999, 1757
8. Che, Y.; Gloer, J. B.; Scott, J. A.; Malloch, D. Tetrahedron Lett. 2004, 45, 6891
9. Bermejo, A.; Figadre, B.; Zafra-Polo, M.; Barrachina, I.; Estornell, E.; Cortes, D. Nat. Prod. Rep. 2005, 22, 269
10. Wu, J.; Li, N.; Hasegawa, T.; Sakai, J.; Kakuta, S.; Tang, W.; Oka, S.; Kiuchi, M.; Ogura, H.; Kataoka, T.; Tomida, A.; Tsuruo, T.; Ando, M. J. Nat. Prod. 2005, 68, 1656
11. Li, Y.; Zhou, F.; Forsyth, C. J. Angew. Chem., Int. Ed. 2007, 46, 279
12. Kladi, M.; Vagias, C.; Papazafiri, P.; Brogi, S.; Tafi, A.; Roussis, V. J. Nat. Prod. 2009, 72, 190
13. Schmitt, A.; Reissig, H.-U. Synlett 1990, 40
14. Schmitt, A.; Reissig, H.-U. Chem. Ber. 1995, 128, 871
15. Schmitt, A.; Reissig, H.-U. Eur. J. Org. Chem. 2000, 3893
16. Larsen, C. H.; Ridgway, B. H.; Shaw, T. J.; Woerpel, K. A. J. Am. Chem. Soc. 1999, 121, 12208
17. Smith, D. M.; Tran, M. B.; Woerpel, K. A. J. Am. Chem. Soc. 2003, 125, 14149
18. Smith, D. M.; Woerpel, K. A. Org. Lett. 2004, 6, 2063
19. Larsen, C. H.; Ridgway, B. H.; Shaw, J. T.; Smith, D. M.; Woerpel, K. A. J. Am. Chem. Soc. 2005, 127, 10879
20. Smith, D. M.; Woerpel, K. A. Org. Biomol. Chem. 2006, 4, 1195
21. Romero, M.; Hernández, L.; Quintero, L.; Sartillo-Piscil, F. Carbohydr. Res. 2006, 341, 2883
22. Sartillo-Meléndez, C.; Cruz-Gregorio, S.; Quintero, L.; Sartillo-Piscil, F. Lett. Org. Chem. 2006, 3, 504
23. Hernández-García, L.; Quintero, L.; Höpfl, H.; Sosa, M.; Sartillo-Piscil, F. Tetrahedron 2009, 65, 139
24. Selected references related to (+), (-)-Jaspine B and epimers: Kuroda, I.; Musman, M.; Ohtani, I. I.; Ichiba, T.; Tanaka, J.; Gravalos, D. G.; Higa, T. J. Nat. Prod. 2002, 65, 1505
25. Bhaket, P.; Morris, K.; Stauffer, C. S.; Datta, A. Org. Lett. 2005, 7, 875
26. Davies, S. G.; Roberts, P. M.; Russell, A. J.; Thomson, J. E. Tetrahedron: Asymmetry 2008, 19, 1027
27. Canals, D.; Mormeneo, D.; Fabrias, G.; Llebaria, A. Bioorg. Med. Chem. 2009, 17, 235
28. Jayachitra, G.; Sudhakar, N.; Anchoori, R. K.; Rao, B. V.; Roy, S.; Banerjee, R. Synthesis 2010, 115
29. Yoshimitsu, Y.; Inuki, S.; Oishi, S.; Fujii, N.; Ohno, H. J. Org. Chem. 2010, 75, 3843
30. Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446
31. Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18
32. Grubbs, R. H. Handbook of Metathesis; Wiley-VCH: Germany, 2003.
33. Chatterjee, A. K.; Choi, T.-L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360
34. Boto, A.; Hernández, R.; Suárez, E. Tetrahedron Lett. 2002, 43, 1821
35. Boto, A.; Hernández, D.; Hernández, R.; Suarez, E. J. Org. Chem. 2003, 68, 5310
36. Boto, A.; Hernández, R.; Montoya, A.; Suarez, E. Tetrahedron Lett. 2004, 45, 1559
37. Boto, A.; Hernández, R.; Montoya, A.; Suárez, E. Eur. J. Org. Chem. 2007, 325
38. Monrad, R. N.; Madsen, R. J. Org. Chem. 2007, 72, 9782
39. Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168
40. Kingsbury, J. S.; Hoveyda, A. H. J. Am. Chem. Soc. 2005, 127, 4510
41. Kim, S.; Lee, T. A.; Song, Y. Synlett 1998, 471
42. Hernández-García, L.; Quintero, L.; Sánchez, M.; Sartillo-Piscil, F. J. Org. Chem. 2007, 72, 8196
43. Hollenberg, D. H.; Watanabe, K. A.; Fox, J. J. Carbohydr. Res. 1975, 42, 241
44. Alper, P. B.; Hendrix, M.; Sears, P.; Wong, C.-H. J. Am. Chem. Soc. 1998, 120, 1965
45. Parr., I. B.; Horenstein, B. A. J. Org. Chem. 1997, 62, 7489