A novel entry to 5a-carba-hexopyranoses from carbohydrates based on a 6-exo-dig radical cyclization: synthesis of 5a-carba-β-D-mannopyranose pentaacetate

Abstract

Carbohydrate-derived 2,3:4,6-diacetonides which are homologated at C-1 by reaction with phenyl acetylide undergo a 6-exo-dig radical cyclization, from a radical located at C-5, to yield highly functionalized cyclohexanes that are correlated with carba-sugars.

References

1. T. Suami and S. Ogawa, Adv. Carbohydr. Chem. Biochem., 1990, 48, 21.
2. G. E. McCasland, S. Furuta and L. J. Durham, J. Org. Chem., 1966, 31, 1516; 1968, 33, 2835; 1968, 33, 2841.
3. T. Iwasa, H. Yamamoto and M. Shibata, J. Antibiot., 1970, 32, 595; T. W. Miller, B. H. Arison and G. Albers-Schonberg, Biotechnol. Bioeng., 1973, 15, 1075.
4. S. Ogawa, in Carbohydrate Mimics: Concepts and Methods, ed. Y. Chapleur, Wiley-VCH, Weinheim, 1998, p. 87; S. Ogawa, in Carbohydrates in Drug Design, ed. Z. J. Witczak and K. A. Nieforth, Marcel Dekker, New York, 1997, p. 433; T. Suami, Top. Curr. Chem., 1990, 154, 257 and references cited therein.
5. S. Ogawa, in Studies in Natural Products Chemistry, ed. A.-U. Rahman, Elsevier Science, 1993, vol. 13, p. 187; T. Suami, Pure Appl. Chem., 1987, 59, 1509.
6. A. V. R. L. Sudha and M. Nagarajan, Chem. Commun., 1998, 925; R. Angelaud and Y. Landais, Tetrahedron Lett., 1997, 38, 8841; R. Verduyn, S. H. van Leeuwen, G. A. van der Marel and J. H. van Boom, Recl. Trav. Chim. Pays-Bas, 1996, 115, 67; H. A. J. Carless and S. S. Malik, J. Chem. Soc., Chem. Commun., 1995, 2447; D. A. Entwistle and T. Hudlicky, Tetrahedron Lett., 1995, 36, 2591; L. Pingli and M. Vandewalle, Synlett, 1994, 228; M. Yoshikawa, N. Murakami, Y. Yokokawa, Y. Inoue, Y. Kuroda and I. Kitagawa, Tetrahedron, 1994, 50, 9619; D. S. Larsen, N. S. Trotter and R. J. Stoodley, Tetrahedron Lett., 1993, 34, 8151; T. K. M. Shing, Y.-X. Cui and Y. Tang, Tetrahedron, 1992, 48, 2349; J. L. Aceña, O. Arjona, R. Fernánde de la Pradilla, J. Plumet and A. Viso, J. Org. Chem., 1992, 57, 1945; S. V. Ley and L. L. Yeung, Synlett, 1992, 291; S. Cai, M. R. Stroud, S. Hakomori and T. Toyokuni, J. Org. Chem., 1992, 57, 6693; R. Blattner and R. J. Ferrier, J. Chem. Soc., Chem. Commun., 1987, 1008.
7. W. B. Motherwell and D. Crich, Free Radical Chain Reactions in Organic Synthesis, Academic Press, London, 1992; D. P. Curran, Synthesis, 1989, 417; D. P. Curran, Synthesis, 1989, 489.
8. H. Redlich, W. Sudau, A. K. Szardenings and R. Vollerthun, Carbohyr. Res., 1992, 226, 57.
9. E. Maudru, G. Singh and R. H. Wightman, Chem. Commun., 1998, 1505.
10. R. J. Ferrier and S. Middleton, Chem. Rev., 1993, 93, 2779; B. Fraser-Reid and R. Tsang, Strategies and Tactics in Organic Synthesis, Academic Press, New York, 1989, vol. 2, p. 123.
11. A. M. Gómez, S. Mantecón, S. Valverde and J. C. López, J. Org. Chem., 1997, 62, 6612; J. C. López, A. M. Gómez and S. Valverde, J. Chem. Soc., Chem. Commun., 1992, 613.
12. J. Gelas and D. Horton, Carbohydr. Res., 1978, 67, 371.
13. J. J. Gaudino and C. S. Wilcox, J. Am. Chem. Soc., 1990, 112, 4374.
14. M. J. Robins, J. S. Wilson and F. Hansske, J. Am. Chem. Soc., 1983, 105, 4059.
15. D. H. R. Barton and S. W. McCombie, J. Chem. Soc., Perkin Trans. 1, 1975, 1574.
16. (a) L. Pingli and M. Vandewalle, Tetrahedron, 1994, 50, 7061; (b) T. Takahashi, H. Kotsubo, T. Namiki and T. Koizumi, J. Chem. Soc., Perkin Trans. 1, 1990, 3065; (c) H. Paulsen, W. von Deyn and W. Röben, Liebigs Ann. Chem., 1984, 433.
17. D. L. J. Clive, P. L. Beaulieu and L. Set, J. Org. Chem., 1984, 49, 1314.
18. R. E. McDevitt and B. Fraser-Reid, J. Org. Chem., 1994, 59, 3250.
19. D. P. Curran, N. A. Porter and B. Giese, Stereochemistry of Radical Reactions, VCH, Weinheim, 1996p. 53.