Ring-opening reactions of iminosugar-derived aziridines: Application to the general synthesis of α-1-C-substituted derivatives of fagomine

Tetrahedron Asymmetry

Volumn 14, Issue 14, 2003, Pages 1969-1972

  Goujon, Jean Yves ^a   Gueyrard, David ^a   Compain, Philippe ^a   Martin, Olivier R ^a   Asano, Naoki ^b  

^a UNIVERSITÉ D'ORLÉANS   (France)

^b HOKURIKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; AMINE; AZIRIDINE DERIVATIVE; BENZYL DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; FAGOMINE; GLYCOSIDE; PHOSPHATE; THIOL DERIVATIVE; TRI 2 BENZYL DEXTRO GLUCAL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHROMATOGRAPHY; CYCLIZATION; PRIORITY JOURNAL; PURIFICATION; RING OPENING; STEREOISOMERISM; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0037484785     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00364-1     Document Type: Article

References (30)

1. For recent reviews, see: (a) Sweeney, J. B. Chem. Soc. Rev. 2002, 31, 247; (b) McCoull, W.; Davis, F. A. Synthesis 2000, 1347.
2. For recent reviews, see: (a) Sweeney, J. B. Chem. Soc. Rev. 2002, 31, 247; (b) McCoull, W.; Davis, F. A. Synthesis 2000, 1347.
3. Stütz A.E. Iminosugars as Glycosidase Inhibitors: Nojirimycin and Beyond. 1999;Wiley-VCH, Weinheim.
4. Asano N., Nash R.J., Molyneux R.J., Fleet G.W.J. Tetrahedron: Asymmetry. 11:2000;1645.
5. Compain P., Martin O.R. Bioorg. Med. Chem. 9:2001;3077.
6. Compain P., Martin O.R. Curr. Top. Med. Chem. 3:2003;541.
7. Schramm V.L., Tyler P.C. Curr. Top. Med. Chem. 3:2003;525.
8. Lee R.E., Smith M.D., Pickering L., Fleet G.W.J. Tetrahedron Lett. 39:1999;8689.
9. Iminosugars: Recent Insights Into Their Bioactivity and Potential As Therapeutic Agents in Curr. Top. Med. Chem.; Martin, O. R.; Compain, P., Eds.; Bentham, Neth., 2003, 3, issue 5.
10. Iminosugars: Recent Insights Into Their Bioactivity and Potential As Therapeutic Agents in Curr. Top. Med. Chem.; Martin, O. R.; Compain, P., Eds.; Bentham, Neth., 2003, 3, issue 5.
11. Nojima H., Kimura I., Fu-Jin C., Sugihara Y., Haruno M., Kato A., Asano N. J. Nat. Prod. 61:1998;397.
12. Taniguchi S., Asano N., Tomino F., Miwa I. Horm. Metab. Res. 30:1998;679.
13. Asano N., Nishida M., Miyauchi M., Ikeda K., Yamamoto M., Kizu H., Kameda Y., Watson A.A., Nash R.J., Fleet G.W.J. Phytochemistry. 53:2000;379.
14. Tong M.K., Ganem B. J. Am. Chem. Soc. 110:1988;312.
15. Paulsen H., Matzke M., Orthen B., Nuck R., Reutter W. Liebigs Ann. Chem. 10:1990;953.
16. Bernet B., Bulusu Murty A.R.C., Vasella A. Helv. Chim. Acta. 73:1990;940.
17. Martin O.R., Xie F., Liu L. Tetrahedron Lett. 36:1995;4027.
18. Martin O.R., Saavedra O. Tetrahedron Lett. 36:1995;799.
19. Désiré J., Dransfield P.J., Gore P.M., Shipman M. Synlett. 2001;1329.
20. Tius M.A., Busch-Petersen J. Tetrahedron Lett. 35:1994;5181.
21. Costantino V., Imperatore C., Fattorusso E., Mangoni A. Tetrahedron Lett. 41:2000;9177.
22. Martin O.R., Liu L., Yang F. Tetrahedron Lett. 37:1996;1991.
23. Boschetti A., Nicotra F., Panza L., Russo G. J. Org. Chem. 53:1988;4181.
24. The alternative regioisomer could not be detected by NMR spectroscopy.
25. Yadav J.S., Subba Reddy B.V., Parimala G., Venkatram Reddy P. Synthesis. 16:2002;2383.
26. No migration of the acyl group to the endocyclic nitrogen occurred as it was unambiguously established by IR and NMR spectral data.
27. For an example of opening of an N-activated aziridine by a phosphate, see: Misiura K., Kinas R.W., Stec W.J., Kusnierczyk H., Radzikowski C., Sonoda A. J. Med. Chem. 31:1988;226.
28. Jefford C.W., Wang J. Tetrahedron Lett. 34:1993;1111.
29. 3 requires 176.1286).
30. 3 requires 160.0973).