Synthesis of functionalized bicyclo[3.1.0]hexanes from aucubin: An access to fused aminocyclopentitols

Helvetica Chimica Acta

Volumn 83, Issue 10, 2000, Pages 2812-2822

  Cachet, Xavier ^a   Deguin, Brigitte ^a   Tillequin, François ^a   Rolland, Yves ^b   Koch, Michel ^a  

^a UNIVERSITÉ PARIS DESCARTES   (France)

^b INSTITUT DE RECHERCHES INTERNATIONALES SERVIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

1 AMINO 2,6 BIS(HYDROXYMETHYL)BICYCLO[3.1.0]HEXANE 2,3,4 TRIOL; AUCUBIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION KINETICS; CHIRALITY; PHYTOCHEMISTRY; SYNTHESIS;

EID: 0033769417     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1522-2675(20001004)83:10<2812::AID-HLCA2812>3.0.CO;2-7     Document Type: Article

References (47)

1. A. Bianco, in 'Studies In Natural Products Chemistry', Ed. Atta-ur-Rahman, Elsevier, Amsterdam, 1990, Vol. 7, p. 439.
2. a) M. Naruto, K. Ohno, N. Naruse, Chem. Lett. 1978, 1419;
3. b) M. Naruto, K. Ohno, N. Naruse, H. Takeuchi, Tetrahedron Lett. 1979, 251;
4. c) W. F. Berkowitz, I. Sasson, P. S. Sampathkumar, J. Hrabie, S. Choudhry, D. Pierce, Tetrahedron Lett. 1979, 1641;
5. d) M. Naruto, K. Ohno, Chem. Lett. 1980, 175;
6. e) W. F. Berkowitz, S. C. Choudhry, J. A. Hrabie, J. Org. Chem. 1982, 47, 824;
7. f) C. Bonini, R. Di Fabio, Tetrahedron Lett. 1982, 23, 5199;
8. g) A. Tixidre, Y. Rolland, J. Garnier, J. Poisson, Heterocycles 1982, 19, 253;
9. h) K. Weinges, G. Braun, B. Oster, Liebigs Ann. Chem. 1983, 2197;
10. i) F. Bonadies, A. Guibbiotti, C. Bonini, Gazz. Chim. Ital. 1985, 115, 45;
11. j) R. Bernini, E. Davini, C. Iavarone, C. Trogolo, J. Org. Chem. 1986, 51, 4600;
12. k) K. Weinges, D. Brunner, Liebigs Ann. Chem. 1986, 54;
13. l) E. Davini, C. Iavarone, C. Trogolo, Heterocycles 1988, 27, 57 and 1557;
14. m) E. Davini, C. Iavarone, F. Mataloni, C. Trogolo, J. Org. Chem. 1988, 53, 2089.
15. C. Bonini, C. Iavarone, C. Trogolo, R. Di Fabio, J. Org. Chem. 1985, 50, 958;
16. K. Weinges, U. Lernhardt, Liebigs Ann. Chem. 1990, 751;
17. K. Weinges, H. J. Ziegler, H. Schick, Liebigs Ann. Chem. 1992, 1213;
18. A. D'Annibale, C. Iavarone, C. Trogolo, Heterocycles 1993, 36, 701;
19. E. Bettelli, P. D'Andrea, S. Mascanzoni, P. Passancantilli, G. Piancatelli, Carbohydr. Res. 1998, 306, 221.
20. M. R. Roby, F. Stermitz, J. Nat. Prod. 1984, 47, 854;
21. Y. Ranarivelo, F. Hotellier, A.-L. Skaltsounis, F. Tillequin, Heterocycles 1990, 31, 1727;
22. H. Franzyk, S. M. Frederiksen, R. S. Jensen, J. Nat. Prod. 1997, 60, 1012;
23. B. Baghdikian, E. Ollivier, R. Faure, L. Debrauwer, P. Rathelot, G. Balansard, J. Nat. Prod. 1999, 62, 211.
24. A. Bianco, M. Guiso, C. Iavarone, R. Marini-Bettolo, C. Trogolo, Tetrahedron 1979, 35, 1121.
25. K. Weinges, S. Haremsa, Liebigs Ann. Chem. 1987, 679;
26. K. Weinges, H. Iatridou, H.-G. Stammler, K. Weiss, Angew. Chem. 1989, 101, 485;
27. K. Weinges, U. Dietz, T. Oeser, H. Irngartinger, Angew. Chem. 1990, 102, 685;
28. K. Weinges, H. Iatridou, U. Diets, Liebigs Ann. Chem. 1991, 893.
29. E. Bourquelot, C. R. Herissey, Acad. Sci. 1902, 134, 1441.
30. a) T. H. Chan, Y. J. Zhang, F. Sauriol, A. W. Thomas, G. M. Strunz, Can. J. Chem. 1987, 65, 1853;
31. b) A. K. Mohammed-Ali, T. H. Chan, A. W. Thomas, B. Jewett, G. M. Strunz, Can. J. Chem. 1994, 72, 2137.
32. A. Bianco, R. A. Mazzei, Tetrahedron Lett. 1997, 38, 6433;
33. H. Franzyk, J. H. Rasmussen, R. A. Mazzei, S. R. Jenssen, Eur. J. Org. Chem. 1998, 2931.
34. X. Cachet, B. Deguin, M. Koch, K. Maklhouf, F. Tillequin, J. Nat. Prod. 1999, 62, 400.
35. H. Morishima, K. Kojiri, T. Yamamoto, T. Aoyagi, H. Nakamura, Y. Iitaka, J. Antibiot. 1989, 42, 1008;
36. J. E. Tropea, G. P. Kaushal, I. Pastuszak, M. Mitchell, T. Aoyagi, R. J. Molyneux, A. D. Elbein, Biochemistry 1990, 29, 10062.
37. B. Ganem, in 'Carbohydrate Mimics', Ed. Y. Chapleur, Wiley-VCH, Weinheim, 1998; p. 239;
38. A. Berecibar, C. Grandjean, A. Siriwardena, Chem. Rev. 1999, 99, 779.
39. S. Ogawa, K. Washida, Eur. J. Org. Chem. 1998, 1929.
40. M. Hudlicky, in 'Oxidations in Organic Chemistry', American Chemical Society, Washington, D.C., 1990, p. 70.
41. A. M. Aleksandrov, R. P. Kashyap, T. J. Pehk, A. E. Petrenko, W. H. Watson, J. Org. Chem. 1993, 58, 1831.
42. E. D. Laganis, B. L. Chenard, Tetrahedron Lett. 1984, 25, 5831;
43. P. A. Bartlett, Y. Nakayawa, C. R. Johnson, S. H. Reich, A. Luis, J. Org. Chem. 1998, 53, 3195;
44. M. Brunner, R. Reinhard, R. Rham, G. Maas, Synlett 1994, 627.
45. E. J. Corey, G. Schmidt, Tetrahedron Lett. 1979, 399.
46. A. Chiaroni, C. Riche, X. Cachet, B. Deguin, M. Koch, F. Tillequin, Acta Crystallogr., Sect. C 2000, 56, 358.
47. T. L. Capson, C. D. Poulter, Tetrahedron Lett. 1984, 25, 3515.