Manganese(III)-mediated radical reactions in carbohydrate chemistry: A new route to 3-deoxy-D-manno-oct-2-ulosonic acid (KDO)

Synlett

Volumn , Issue 15, 2004, Pages 2728-2731

  Hartmann, Klaus ^a   Kim, Boo Geun ^a   Linker, Torsten ^a  

^a UNIVERSITY OF POTSDAM   (Germany)

Author keywords

Carbohydrates; Lactones; Natural products; Radical reactions; Transition metals

Indexed keywords

3 DEOXY MANNO OCTULOSONIC ACID; ACETIC ACID; ALKENE; CARBOHYDRATE; LACTONE; MALONIC ACID; MANGANESE; NATURAL PRODUCT; TRANSITION ELEMENT;

ARTICLE; CARBOHYDRATE ANALYSIS; CHEMICAL REACTION; DIASTEREOISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; RADICAL REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 10844287836     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-835648     Document Type: Article

References (30)

1. Recent reviews: (a) Snider, B. B. Chem. Rev. 1996, 96, 339.
2. (b) Melikyan, G. G. Org. React. 1997, 49, 427.
3. (c) Linker, T. J. Prakt. Chem. 1997, 339, 488.
4. (d) Snider, B. B. In Radicals in Organic Synthesis, Vol. 1; Renaud, P.; Sibi, M., Eds.; Wiley-VCH: Weinheim, 2001, 198.
5. Recent reviews: (a) Nair, V.; Mathew, J.; Prabhakaran, J. Chem. Soc. Rev. 1997, 127.
6. (b) Linker, T. In Radicals in Organic Synthesis, Vol. 1; Renaud, P.; Sibi, M., Eds.; Wiley-VCH: Weinheim, 2001, 219.
7. (c) Nair, T.; Balagopal, L.; Rajan, R.; Mathew, J. Acc. Chem. Res. 2004, 37, 21.
8. (a) Linker, T.; Hartmann, K.; Sommermann, T.; Scheutzow, D.; Ruckdeschel, E. Angew. Chem., Int. Ed. Engl. 1996, 35, 1730.
9. (b) Linker, T.; Sommermann, T.; Kahlenberg, F. J. Am. Chem. Soc. 1997, 119, 9377.
10. (c) Gyóllai, V.; Schanzenbach, D.; Somsák, L.; Linker, T. Chem. Commun. 2002, 1294.
11. (d) Linker, T. J. Organomet. Chem. 2002, 661, 159.
12. Recent Review: Li, L.-S.; Wu, Y.-L. Curr. Org. Chem. 2003, 7, 447.
13. Aspinall, G. O.; Carpenter, R. C.; Khondo, L. Carbohydr. Res. 1987, 165, 281.
14. (a) Allegretti, M.; D'Annibale, A.; Trogolo, C. Tetrahedron 1993, 49, 10705.
15. (b) Bosman, C.; D'Annibale, A.; Resta, S.; Trogolo, C. Tetrahedron 1994, 50, 13847.
16. (c) Linker, T.; Linker, U. Angew. Chem. Int. Ed. 2000, 39, 902.
17. (a) Linker, U.; Kersten, B.; Linker, T. Tetrahedron 1995, 57, 9917.
18. (b) Linker, T.; Kersten, B.; Linker, U.; Peters, K.; Peters, E.-M.; von Schnering, H. G. Synlett 1996, 468.
19. (a) Heiba, E. I.; Dessau, R. M.; Rodewald, P. G. J. Am. Chem. Soc. 1974, 96, 7977.
20. (b) Fristad, W. E.; Peterson, J. R. J. Org. Chem. 1985, 50, 10.
21. (c) Surzur, J.-M.; Bertrand, M. P. Pure Appl. Chem. 1988, 60, 1659.
22. (a) Julia, M. Acc. Chem. Res. 1971, 4, 386.
23. (b) Curran, D. P.; Morgan, T. M.; Schwartz, E.; Snider, B. B.; Dombroski, M. A. J. Am. Chem. Soc. 1991, 113, 6607.
24. Reviews on stereoselective radical reactions: (a) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: Weinheim, 1996.
25. (b) Giese, B. In Radicals in Organic Synthesis, Vol. 1; Renaud, P.; Sibi, M., Eds.; Wiley-VCH: Weinheim, 2001, 381.
26. (c) Sibi, M. P.; Manyem, S.; Zimmerman, J. Chem. Rev. 2003, 103, 3263.
27. Peters, K.; Peters, E.-M.; Hartmann, K.; Kim, B. G.; Linker, T. Z. Kristallogr. - New Cryst. Struct 2004, 279, in press.
28. 10: C, 51.34; H, 5.92. Found: C, 51.37; H, 5.72.
29. (a) Collins, P. M.; Overend, W. G.; Shing, T. J. Chem. Soc., Chem. Commun. 1981, 1139.
30. (b) Railton, C. J.; Clive, D. L. J. Carbohydr. Res. 1996, 257, 69.