A new and concise synthesis of 3-deoxy-D-arabino-2-heptulopyranosonic acid (DAH) and derivatives through the radical chemistry of Barton esters

Tetrahedron Letters

Volumn 38, Issue 3, 1997, Pages 367-370

  Barton, Derek H R ^a   Liu, Wansheng ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE DERIVATIVE;

ARTICLE; CARBOHYDRATE SYNTHESIS; DRUG SYNTHESIS; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031021499     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02331-3     Document Type: Article

References (29)

1. Haslam, E. The Shikimate Pathway; John Wiley & Sons: New York, 1974.
2. Weiss, U.; Edwards, J. M. The Biosynthesis of Aromatic Compounds; John Wiley & Sons: New York, 1980.
3. Myrvold, S.; Reimer, L. M.; Pompliano, D. L.; Frost, J. W. J. Am. Chem. Soc. 1989, 111, 1861.
4. (a) Draths, K. M.; Frost, J. W. J. Am. Chem. Soc. 1990, 112, 1657.
5. (b) Sugai, T.; Shen, G.-J.; Ichikawa, Y.; Wong, C.-H. J. Am. Chem. Soc. 1993, 115, 413.
6. (c) Augé, C.; Delest, V. Tetrahedron: Asymmetry 1995, 6, 863.
7. (a) Ramage, R.; MacLeod, A. M.; Rose, G. W. Tetrahedron 1991, 47, 5625.
8. (b) Dondoni, A.; Marra, A.; Merino, P. J. Am. Chem. Soc. 1994, 116, 3324.
9. (c) López-Herrera, F. J.; Sarabia-García, F. Tetrahedron Lett. 1994, 35, 6705.
10. (d) Johnson, C. R.; Kozak, J. J. Org. Chem. 1994, 59, 2910.
11. (a) Reimer, L. M.; Conley, D. L.; Pompliano, D. L.; Frost, J. W. J. Am. Chem. Soc. 1986, 108, 8010.
12. (a) Barton, D. H. R.; Crich, D.; Motherwell, W. B. Tetrahedron Lett. 1983, 24, 4979.
13. (b) Barton, D. H. R.; Crich, D.; Kretzschmar, G. Tetrahedron Lett. 1984, 25, 1055.
14. (c) Barton, D. H. R.; Crich, D.; Motherwell, W. B. Tetrahedron 1985, 41, 3901.
15. (d) For a recent review, see: Barton, D. H. R.; Parekh, S. I. Half a Century of Free Radical Chemistry; Cambridge University Press, 1993.
16. Barton, D. H. R.; Chern, C.-Y.; Jaszberenyi, J. Cs. Tetrahedron 1995, 51, 1867.
17. (a) Barton, D. H. R.; Géro, S. D.; Quiclet-Sire, B.; Samadi, M. Tetrahedron: Asymmetry 1994, 5, 2123.
18. (b) Giese, B.; Linker, T. Synthesis 1992, 46.
19. (c) Giese, B.; Carboni, B.; Gobel, T.; Muhn, R.; Wetterich, F. Tetrahedron Lett. 1992, 33, 2673.
20. (d) Branchaud, B. P.; Meier, M. S. J. Org. Chem. 1989, 54, 1320.
21. Regeling, H.; Rouville, E. de; Chittenden, G. J. F. Recl. Trav. Chim. Pays-Bas 1987, 106, 461.
22. Barton, D. H. R.; Camara, J.; Cheng, X.; Géro, S. D.; Jaszberenyi, J. Cs.; Quiclet-Sire, B. Tetrahedron 1992, 48, 9261.
23. Barton, D. H. R.; Jaszberenyi, J. Cs.; Liu, W.; Shinada, T. Tetrahedron 1996, 52, 2717.
24. (a) Barton, D. H. R.; Gateau-Olesker, A.; Géro, S. D.; Lacher, B.; Tachdjian, C.; Zard, S. Z. Tetrahedron 1993, 49, 4589.
25. (b) For a recent review, see: Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: New York, 1996.
26. +) requires 317.1600.
27. +) requires 259.0794.
28. +) requires 427.1216.
29. Shing, T. K. M. Tetrahedron: Asymmetry 1994, 5, 2405.