n-Pentenyl esters facilitate an oxidative alternative to the Ferrier rearrangement. An expeditious route to sucrose

Journal of the Chemical Society, Chemical Communications

Volumn , Issue 2, 1992, Pages 94-96

  López, J Cristóbal ^a   Fraser Reid, Bert ^a  

^a DUKE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0007771906     PISSN: 00224936     EISSN: None     Source Type: Journal    
DOI: 10.1039/C39920000094     Document Type: Article

References (34)

1. R. J. Ferrier, Adv. Carbohydr. Chem. Biochem., 1969 199.
2. R. J. Ferrier and N. Prasad, J. Chem. Soc. C, 1969 570.
3. B. Fraser-Reid, Acc. Chem. Res., 1985, 18, 347.
4. I. Lundt and C. Pedersen, Acta Chem. Scand., 1970, 24, 240.
5. G. Descotes and J.-C. Martin, Carbohydr. Res., 1977, 56, 168.
6. G. Grynkiewicz, W. Priebe and A. Zamojski, Carbohydr. Res., 1979, 68, 33.
7. A. F. Hadfield and A. C. Sartorelli, Carbohydr. Res., 1982, 101, 240.
8. J. C. Lopez and B. Fraser-Reid, J. Chem. Soc., Chem. Commun., 1991 159.
9. H. Kunz, P. Wernig and M. Schultz, Synlett., 1990 631.
10. D. R. Mootoo, P. Konradsson, U. Udodong and B. Fraser-Reid, J. Am. Chem. Soc., 1988, 110, 5583.
11. D. R. Mootoo, V. Date and B. Fraser-Reid, J. Am. Chem. Soc., 1988, 110, 5583.
12. B. Fraser-Reid, P. Konradsson, D. R. Mootoo and U. Udodong, J. Chem. Soc., Chem. Commun., 1988 823.
13. H. N. mereyala and G. V. Reddy, 17th IUPAC International Symposium on the Chemsitry of Natural Products, New Delhi, India, February, 4–9, 1990;.
14. G. H. Veeneman, S. H. van Leeuwen and J. H. van Boom, Tetrahedron Lett., 1990, 31, 1331.
15. G. H. Veeneman and J. H. van Boom, Tetrahedron Lett., 1990, 31, 275.
16. R. W. Friesen and S. Danishefsky, J. Am. Chem. Soc., 1989, 111, 6656.
17. K. Suzuki, G. A. Sulikowski, R. W. Friesen and S. Danishefsky, J. Am. Chem. Soc., 1990, 112, 8895.
18. R. W. friesen and S. Danishefsky, Tetrahedron, 1990, 111, 103.
19. B. Fraser-Reid, Z. Wu, U. Udodong and H. Ottosson, J. Org. Chem., 1990 in the press.
20. B. Fraser-Reid, D. L. Walker, S. Y.-K. Tam and N. L. Holder, Can J. Chem., 1973, 51, 3950.
21. B. Neises and W. Steglich, Angew. Chem., 1978, 90, 556.
22. B. Neises and W. Steglich, Angew. Chem., Int. Ed. Engl., 1978 522.
23. D. E. Iley and B. Fraser-Reid, J. Am. Chem. Soc., 1975, 97, 2563.
24. B. Fraser-Reid and D. E. Iley, Can. J. Chem., 1979, 57, 645.
25. R. U. Lemieus and A. R. Morgan, Can. J. Chem., 1965, 43, 2190.
26. A. R. Feast, W. G. Overend and N. A. Williams, Chem. Commun., 1965 7378.
27. H. kessler, A. Kling and M. Kottenhahn, Angew. Chem., 1990, 95, 452.
28. H. kessler, A. Kling and M. Kottenhahn, Angew. Chem., Int. Ed. Engl., 1990, 29, 425.
29. O. Mitsunobu, Synthesis, 1981 1.
30. W. W. Binkley and M. L. Wolfrom, J. Am. Chem. Soc., 1946, 68, 2171.
31. D. E. Iley, M. Sc. Thesis, University of Waterloo, 1975.
32. J. Thiem, in Trends in Synthetic Carbohydrate Chemistry, ed. D. Horton, L. D. Hawkins and G. J. McGarvey, ACS Symposium Series 386, American Chemical Society, Washington, DC, 1989, ch. 8;.
33. J. Thiem, H. karl and J. Schwentner, Synthesis, 1978 696.
34. J. Thiem and W. Klaffke, Carbohydr. Res., 1988, 174, 201.