Radical cyclisation of carbohydrate alkynes: synthesis of highly functionalised cyclohexanes and carbasugars

Abstract

Carbohydrate alkynes undergo 6-exo radical cyclisation to afford cyclohexanes resulting in the synthesis of carbasugars.

References

1. R. J. Ferrier and S. Middleton, Chem. Rev., 1993, 93, 2779.
2. H. O. L. Fischer and J. M. Grosheintz, J. Am. Chem. Soc., 1948, 70, 1476; H. O. L. Fischer and B. Iselin, J. Am. Chem. Soc., 1948, 70, 3946.
3. For excellent reviews on radical cyclisation reactions see: (a) B. Giese, B. Kopping, T. Gobel, J. Dickhaut, G. Thoma, K. J. Kulicke and F. Trach, Org. React., 1996, 48 ch. 2; (b) W. B. Motherwell and D. Crich, Free Radical Chain Reactions in Organic Synthesis, Academic Press, New York, 1992.
4. B. Fraser-Reid and R. Tsang, Strategies and Tactics in Organic Synthesis, Academic Press, New York, 1989, vol. 2.
5. G. Büchi and H. Wüest, J. Org. Chem., 1979, 44, 546; M. D. Bachi and C. Hoornaert, Tetrahedron Lett., 1982, 23, 2502; D. L. J. Clive, P. L. Beaulieu and L. Set, J. Org. Chem., 1984, 49, 1313; J. K. Crandell and W. I. Michaley, J. Org. Chem., 1984, 49, 4244; G. Just and G. Sacripante, Can. J. Chem., 1987, 65, 104; A. V. Rama Rao, J. S. Yadav, C. S. Rao and S. Chandrasekhar, J. Chem. Soc., Perkin Trans. 1, 1990, 1211; C. K. Sha, T. S. Jean and D. C. Wang, Tetrahedron Lett., 1990, 31, 3745; D. L. Boger and R. J. Mathvink, J. Am. Chem. Soc., 1990, 112, 4003; T. Honda, M. Satoh and Y. Kobayashi, J. Chem. Soc., Perkin Trans. 1, 1992, 1557; J. Marco-Contelles, Synth Commun., 1994, 24, 1293; J. Marco-Contelles, M. Bernabe, D. Ayala and B. Sanchez, J. Org. Chem., 1994, 59, 1234 this details a 6-endo-dig cyclisation; R. E. McDevitt and B. Fraser-Reid, J. Org. Chem., 1994, 59, 3250.
6. A. L. J. Beckwith, Tetrahedron, 1981, 37, 3073; A. L. J. Beckwith and C. J. Easton, J. Am. Chem. Soc., 1981, 103, 615; V. Malatesta and K. U. Ingold, J. Am. Chem. Soc., 1981, 103, 609; A. L. J. Beckwith and C. H. Schiesser, Tetrahedron, 1985, 41, 3925; P. R. Jenkins, M. C. R. Symons, S. E. Booth and C. J. Swain, Tetrahedron Lett., 1992, 33, 3545.
7. B. Mekki, G. Singh and R. H. Wightman, Tetrahedron Lett., 1991, 32, 5143 and references cited therein.
8. G. Stork and T. Takahashi, J. Am. Chem. Soc., 1977, 99, 1275.
9. S. Jiang, G. Singh and R. H. Wightman, Chem. Lett., 1996, 67.
10. P. J. Garegg and B. Samuelsson, J. Chem. Soc., Perkin Trans. 1, 1980, 2866.
11. J.-C. Malanda and A. Doutheau, J. Carbohydr. Chem., 1993, 12, 999.
12. W. T. Borden and A. Nicolaides, J. Am. Chem. Soc., 1991, 113, 6750 and refs. therein.
13. L. Pingli and M. Vandewalle, Tetrahedron, 1994, 50, 7061; L. Pingli and M. Vandewalle, Synlett., 1994, 228.