Nitrile oxide/isoxazoline approach to higher monosaccharides: synthesis of 7-deoxy-nonose and -decose derivatives 1

Abstract

7-Deoxy-D-ribo-D-galacto - and 7-deoxy-D-xylo-D-galacto-decopy ranoside derivatives 11 and 12 have been prepared by a sequence involving diastereoselective cycloaddition of 2,3-O-isopropylidene-D-glyceronitrile oxide to D-galactose-derived alkene 3 to afford the isoxazoline 5 as the major adduct, followed by reductive hydrolytic cleavage of the isoxazoline and reduction of the resulting β-hydroxy ketone. The configuration of the new chiral centre (C-8) in compounds 11 and 12 is established by NMR analysis of their 6,8-O-isopropylidene derivatives 13 and 14. 7-Deoxy-L-threo-D-galacto- and 7-deoxy-D-erythro-D-galacto-non opyranosides 15 and 16 are prepared similarly from alkene 3 and ethoxycarbonylformonitrile oxide via isoxazolines 8 and 17, and β-hydroxy ketone 18. The 6,7-dideoxynon-6-enos-8-ulose 19 is also prepared from isoxazoline 5.

References

1. Preliminary communication: R. M. Paton and A. A. Young, J. Chem. Soc., Chem. Commun., 1991, 132.
2. For reviews of higher sugars see: J. S. Brimacombe, in Studies in Natural Products Chemistry, ed. Atta-ur-Rahman, Elsevier, Amsterdam, 1989, vol. 4, pp. 157–193; A. Zamoski and S. Jarosz, Pol. J. Chem., 1992, 66, 525; G. Casiraghi and G. Rassu, in Studies in Natural Products Chemistry, ed. Atta-ur-Rahman, Elsevier, Amsterdam, 1992, vol. 11, pp. 429–480.
3. Y. Araki, T. Endo, M. Tanji, Y. Arai and Y. Ishido, Tetrahedron Lett., 1988, 29, 2335; A. G. Meyers, D. Y. Gin and K. L. Widdowson, J. Am. Chem. Soc., 1991, 113, 9661; A. G. Meyers, D. Y. Gin and D. H. Rogers, J. Am. Chem. Soc., 1993, 115, 2036.
4. M. D. Bedarski, H. J. Waldmann and G. M. Whitesides, Tetrahedron Lett., 1986, 27, 5807.
5. T. Suami, H. Sasai and K. Matsuno, Chem. Lett., 1983, 819; T. Suami, H. Sasai, K. Matsuno and N. Suzuki, Carbohydr. Res., 1985, 143, 85; M. P. McGuire, P. L. Feldman and H. Rapoport, J. Org. Chem., 1990, 55, 948.
6. G. Casiraghi, L. Colombo, G. Rassu and P. Spanu, J. Org. Chem., 1991, 56, 2135; G. Rassu, P. Spanu, G. Casiraghi and L. Pinna, Tetrahedron, 1991, 47, 8025.
7. inter alia J. A. Secrist and K. D. Barnes, J. Org. Chem., 1980, 45, 4526; J. Brimacombe, R. Hanna, A. K. M. S. Kabir, F. Bennet and I. D. Taylor, J. Chem. Soc., Perkin Trans. 1, 1986, 815; J. S. Brimacombe, G. McDonald and M. Abdur Rahman, Carbohydr. Res., 1990, 205, 422; S. Jarosz, D. Mootoo and B. Fraser-Reid, Carbohydr. Res., 1986, 147, 59; S. Jarosz, Carbohydr. Res., 1992, 224, 73.
8. J. S. Brimacombe, A. K. M. S. Kabir and F. Bennett, J. Chem. Soc., Perkin Trans. 1, 1986, 1677; S. Jarosz, Carbohydr. Res., 1988, 183, 21; M. Bessodes, D. Komiotis and K. Antonakis, J. Chem. Soc., Perkin Trans. 1, 1989, 41.
9. A. Dondoni, G. Fantin, M. Fogagnolo, A. Medici and P. Pedrini, J. Org. Chem., 1989, 54, 693; A. Dondoni, Phosphorus Sulfur Silicon Relat. Elem., 1989, 43, 25; Pure Appl. Chem., 1990, 62, 643.
10. N. Ikemoto and S. L. Schreiber, J. Am. Chem. Soc., 1992, 114, 2524.
11. S. J. Danishefsky, S. L. DeNinno, S.-H. Chen, L. Boisvert and M. Barbachyn, J. Am. Chem. Soc., 1989, 111, 5810 and references therein.
12. S. Jenanathan and P. Vogel, J. Org. Chem., 1991, 56, 1133; Tetrahedron Lett., 1993, 34, 4209.
13. J. A. Marshall, S. Beaudoin and K. Lewinski, J. Org. Chem., 1993, 58, 5876.
14. For reviews of nitrile oxide–isoxazoline methodology see (a) A. P. Kozikowski, Acc. Chem. Res., 1984, 17, 410; (b) V. Jäger, I. Müller, R. Schohe, M. Frey, R. Ehrler, B. Häfele and D. Schröter, Lect. Heterocycl. Chem., 1985, 7, 79; (c) D. P. Curran, Adv. Cycloaddit., 1988, 1, 129; (d) K. B. G. Torssell, Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis, VCH, Weinheim, 1988; (e) S. Kanemasa and O. Tsuge, Heterocycles, 1990, 30, 719; (f) P. Grünanger and P. Vita-Finzi, Isoxazoles: The Chemistry of Heterocyclic Compounds, Wiley, New York, 1991, vol. 49, Part 1, p. 572.
15. P. Caramella and P. Grünanger, in 1,3-Dipolar Cycloaddition Chemistry, ed. A. Padwa, Wiley, New York, 1984, ch. 3.
16. R. H. Jones, G. C. Robinson and E. J. Thomas, Tetrahedron, 1984, 40, 177.
17. G. S. Skinner, J. Am. Chem. Soc., 1924, 46, 731.
18. A. J. Blake, R. O. Gould, R. M. Paton and A. A. Young, J. Chem. Res., 1993, (S) 482; (M) 3173.
19. V. Jäger and R. Schohe, Tetrahedron, 1984, 40, 2199.
20. A. J. Blake, G. Kirkpatrick, K. E. McGhie, R. M. Paton and K. J. Penman, J. Carbohydr. Chem., 1994, 13, 409 and references therein.
21. A. J. Blake, E. C. Boyd, R. O. Gould and R. M. Paton, J. Chem. Soc., Perkin Trans. 1, 1994, 2841.
22. K. N. Houk, H. Y. Duh, Y.-D. Wu and S. R. Moses, J. Am. Chem. Soc., 1986, 108, 2754.
23. P. G. Baraldi, A. Baro, S. Benetti, S. Manfredini and D. Simoni, Synthesis, 1987, 276.
24. S. H. Andersen, N. B. Das, R. D. Jurgensen, G. Kjeldsen, J. S. Knudsen, S. C. Sharma and K. B. G. Torssell, Acta Chem. Scand., Ser. B, 1982, 36, 1.
25. A. P. Kozikowski and M. Adamczyk, Tetrahedron Lett., 1982, 23, 3123.
26. J. G. Buchanan, A. R. Edgar, D. I. Rawson, P. Shahidi and R. H. Wightman, Carbohydr. Res., 1982, 100, 75.
27. S. Auricchio and A. Ricca, Tetrahedron, 1987, 43, 3983.
28. R. W. Hoffmann, G. Eichler and A. Endesfelder, Liebigs Ann. Chem., 1983, 2000.