Enantiospecific synthesis of shikimic acid from D-mannose: Formation of a chiral cyclohexene by intramolecular olefination of a carbohydrate-derived intermediate

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue , 1984, Pages 905-908

  Fleet, George W J ^a   Shing, Tony K M ^a   Warr, Steven M ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049112453     PISSN: 14727781     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19840000905     Document Type: Article

References (26)

1. R. J. Ferner, P. Prasit, and P. C. Tyler, J. Chem. Soc., Perkin Trans. 1, 1983, 1641 and references cited therein
2. S. Hanessian, Total Synthesis of Natural Products: The Chiron Approach, Pergamon, Oxford, 1983
3. A. T. Nielsen and W. J. Houlihan, Org. React., 1968, 16, 47
4. G. Jones, Org. React., 1967, 15, 204
5. P. M. Collins, W. G. Overend, and T. K. M. Shing, J. Chem. Soc., Chem. Commun, 1982, 297
6. L. D. Cama and B. D. Christensen, J. Am. Chem. Soc., 1978,100,8006
7. W. S. Wadsworth, Org. React., 1977, 25, 73
8. U. Weiss and J. M. Edwards, The Biosynthesis of Aromatic Compounds, Wiley, New York, 1980
9. E. Haslam, The Shikimate Pathway, Wiley, New York, 1974
10. A. Ganem, Tetrahedron, 1978, 34, 3353
11. M. Koreeda and M. A. Ciufolini, J. Am. Chem. Soc., 1982, 104, 2308
12. C. D. Snyder and H. Rapoport, J. Am. Chem. Soc., 1974, 95, 7821
13. K. E. Coblens, V. B. Muralidharen, and B. Ganem, J. Org. Chem., 1982, 47, 5041
14. H. J. Bestmann and H. A. Heid, Angew. Chem., Int. Ed. Engl., 1971, 10, 336
15. M. Yoshikawa, Y. Ikeda, H. Kayakiri, and I. Kitagawa, Heterocycles, 1982, 17, 209.
16. J. Cleophax, J. Leboul, D. Mercier, A. Gaudemer, and S. DovGero, Bull. Soc. Chim. Fr., 1973, 2992
17. G. W. J. Fleet and T. K. M. Shing, J. Chem. Soc., Chem. Commun., 1983, 849
18. R. L. Whistler and M. L. Wolfrom, Methods Carbohydr. Chem., 1963, 2, 319
19. J. S. Brimacombe, F. Hunedy, and L. C. N. Tucker, J. Chem. Soc. C, 1968, 1381
20. G. Ohrui and S. Emimoto, Tetrahedron Lett., 1975, 2765
21. R. L. Whistler and J. N. BeMiller, Methods Carbohydr. Chem., 1980, 8, 173
22. S. S. Shaik, J. Am. Chem. Soc., 1983, 105, 4359
23. V. K. Iyer and J. P. Horwitz, J. Org. Chem., 1982, 47, 644 and references cited therein
24. H. O. L. Fischer and G. Dangschat, Helv. Chim. Acta, 1934,17,1196,1200
25. H. O. L. Fischer and G. Dangschat, Helv. Chim. Acta, 1935,18,1206
26. J. Boutagy and R. Thomas, Chem. Rev., 1974, 74, 87