Synthesis of KDO Using Indium-Mediated Allylation of 2,3:4,5-Di-O-isopropylidene-D-arabinose in Aqueous Media

Journal of Organic Chemistry

Volumn 59, Issue 13, 1994, Pages 3714-3715

  Gao, Jinming ^a   Härter, Ralph ^a   Gordon, Dana M ^a   Whitesides, George M ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001074997     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00092a040     Document Type: Article

References (32)

1. Unger, F. M. Adu. Carbohydr. Chem. Biochem. 1981, 38, 323.
2. Paulsen, H.; Hoeffgen, E. C.; Brenken, M. ACS Symp. Ser. 1993, 519, 132.
3. Coutrot, Ph.; Grison, C.; Tabyaoui, M. Tetrahedron Lett. 1993, 34, 5089.
4. Dondoni, A.; Merino, P. J. Org. Chem. 1991, 56, 5294.
5. Smith, D. B.; Wang, Z.; Schreiber, S. L. Tetrahedron 1990, 46, 4793.
6. Esswein, A.; Betz, R.; Schmidt, R. R. Helv. Chim. Acta 1989, 72, 213.
7. Branchaud, B. P.; Meier, M. S. J. Org. Chem. 1989, 54, 1320.
8. Danishefsky, S. J.; DeNinno, M. P.; Chen, S. J. Am. Chem. Soc. 1988,110, 3929.
9. Danishefsky, S. J.; Pearson, W. H.; Segmuller, B. E. J. Am. Chem. Soc. 1985, 107, 1280.
10. Sugai, T.; Shen, G. J.; Ichikawa, Y.; Wong, C.-H. J. Am. Chem. Soc. 1993, 115, 413.
11. Bednarski, M. D.; Crans, D. C.; DiCosimo, R.; Simon, E. S.; Stein, P. D.; Whitesides, G. M.; Schneider, M. J. Tetrahedron Lett. 1988, 29, 427.
12. Augé, C.; Gautheron, C.; David, S.; Malleron, A.; Cavayé, B.; Bouxom, B. Tetrahedron 1990, 46, 201.
13. Chao, L. C.; Rieke, R. D. J. Org. Chem. 1975, 40, 2253.
14. Petrier, C.; Einhorn, J.; Luche, J. L. Tetrahedron Lett. 1985, 26, 1449.
15. Einhorn, C.; Luche, J. L. J. Organomet. Chem. 1987, 322, 177.
16. Araki, S.; Ito, H.; Butsugan, Y. J. Org. Chem. 1988, 53, 1831.
17. Araki, S.; Ito, H.; Butsugan, Y. Synth. Commun. 1988,18, 453.
18. Wu, S.; Huang, B.; Gao, X. Synth. Commun. 1990, 20, 1279.
19. Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7017.
20. Schmid, W.; Whitesides, G. M. J. Am. Chem. Soc. 1991,113, 6674.
21. Chan, T. H.; Li, C. J. J. Chem. Soc., Chem. Commun. 1992,747.
22. Kim, E.; Gordon, D. M.; Schmid, W.; Whitesides, G. M. J. Org. Chem. 1993, 58, 5500.
23. Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1993, 58, 7937.
24. Binder, W. H.; Prenner, R. H.; Schmid, W. Tetrahedron 1994,50, 749.
25. Zinner, H.; Wittenburg, E.; Rembarz, G. Chem. Ber. 1959, 92, 1614.
26. Villieras, J. and Rambaud, M. Org. Synth. 1987, 66, 220.
27. Csuk, R.; Hugener, M.; Vasella, A. Helv. Chim. Acta 1988, 71, 609.
28. Baumberger, F.; Vasella, A. Helv. Chim. Acta 1986, 69, 1205.
29. Chérest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 2199.
30. Anh, N. T. Top. Curr. Chem. 1980,88,146.
31. Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1984, 23, 556.
32. Prenner, R. H.; Binder, W. H.; Schmid, W. Liebigs Ann. Chem. 1994, 73.