Total synthesis of deoxymannojirimycin and D-mannolactam via carbonylation of 5-vinyloxazolidin-2-ones

Tetrahedron

Volumn 59, Issue 3, 2003, Pages 281-286

  Knight, Julian G ^a   Tchabanenko, Kirill ^a  

^a NEWCASTLE UNIVERSITY   (United Kingdom)

Author keywords

Carbonylation; D mannolactam; Deoxymannojirimycin

Indexed keywords

1 DEOXYMANNONOJIRIMYCIN; 5 VINYLOXAZOLIDIN 2 ONE; 6 (TERT BUTYLDIMETHYLSILYLOXYMETHYL) 3,6 DIHYDRO 1H PYRIDIN 2 ONE; DEXTRO MANNOLACTAM; DEXTRO SERINE; OXAZOLIDINONE DERIVATIVE; PALLADIUM; PIPERIDINE DERIVATIVE; PYRIDONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBONYLATION; CATALYST; CHEMICAL REACTION; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0037434027     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01534-X     Document Type: Article

References (30)

1. For reviews which include piperidine alkaloids, see: (a) Pinder A.R. Nat. Prod. Rep. 9:1992;491-504 (b) Numata A., Ibuka T. Brossi A. The Alkaloids. Vol. 31:1987;Academic, New York. Chapter 6.
2. For reviews which include piperidine alkaloids, see: (a) Pinder A.R. Nat. Prod. Rep. 9:1992;491-504 (b) Numata A., Ibuka T. Brossi A. The Alkaloids. Vol. 31:1987;Academic, New York. Chapter 6.
3. For more specific information on hydroxylated piperidines, see the following article and references within: Fleet G.W.J., Fellows L.E., Winchester B. Plagiarising Plants: Aminosugars as a Class of Glycosidase Inhibitors. Ciba Foundation Symposium 154. Ciba Foundation Symposium 154. 1990;Wiley, Chichester. pp 112-115.
4. Elbein A.D. Ann. Rev. Biochem. 56:1987;497-534.
5. For isolation see: Fellows L.E., Bell E.A., Lynn D.G., Pilkiewicz F., Miura I., Nakanishi K. J. Chem. Soc., Chem. Commun. 1979;977-978.
6. Fuhrmann U., Bause E., Legler G., Ploegh H. Nature. 307:1984;755-758.
7. Evans S.V., Fellows L.E., Shing T.K.M., Fleet G.W.J. Phytochemistry. 24:1985;1953-1955.
8. Fleet G.W.J., Ramsden N.G., Witty D.R. Tetrahedron. 45:1989;319-326.
9. Yokoyama H., Otaya K., Koboyashi H., Miyazawa M., Yamaguchi S., Hirai Y. Org. Lett. 2:2000;2427-2429.
10. Izquierdo Cubero I., Lopez-Espinosa M.T.P., Richardson A.C., Suarez Ortega M.D. Carbohydr. Res. 242:1993;109-118.
11. De Raadt A., Stuetz A.E. Tetrahedron Lett. 33:1992;189-192.
12. Bernotas R.C., Ganem B. Tetrahedron Lett. 26:1985;1123-1126.
13. Le Merrer Y., Poitout L., Depezay J.-C., Dosbaa I., Geoffroy S., Foglietti M.-J. Bioorg. Med. Chem. 5:1997;519-533.
14. Cook G.R., Beholz L.G., Stille J.R. J. Org. Chem. 59:1994;3575-3584.
15. Meyers A.I., Andres C.J., Resek J.E., Woodall C.C., McLaughlin M.A., Lee P.H., Price D.A. Tetrahedron. 55:1999;8931-8952.
16. Straub A., Effenberger F., Fischer P. J. Org. Chem. 55:1990;3926-3932.
17. Asano K., Hakogi T., Iwama S., Katsumura S. Chem. Commun. 1999;41-42.
18. Haukaas M.H., O'Doherty G.A. Org. Lett. 3:2001;401-404.
19. Liao L.-X., Wang Z.-M., Zhang H.-X., Zhou W.-S. Tetrahedron: Asymmetry. 10:1999;3649-3657.
20. Johnson C.R., Golebiowski A., Schoffers E., Sundram H., Braun M.P. Synlett. 1995;313-314.
21. Hudlicky T., Rouden J., Luna H., Allen S. J. Am. Chem. Soc. 116:1994;5099-5107.
22. Wu X.-D., Khim S.-K., Zhang X., Cederstrom E.M., Mariano P.S. J. Org. Chem. 63:1998;841-859.
23. Xu Y.-M., Zhou W.-S. J. Chem. Soc., Perkin Trans. 1. 1997;741-746.
24. Knight J.G., Ainge S.W., Harm A.M., Harwood S.J., Maughan H.I., Armour D.R., Hollinshead D.M., Jaxa-Chamiec A.A. J. Am. Chem. Soc. 122:2000;2944-2945.
25. Knight J.G., Tchabanenko K. Tetrahedron. 58:2002;6659-6664.
26. Kang M., Park J., Konradi A.W., Pedersen S.F. J. Org. Chem. 61:1996;5528-5532.
27. See e.g. Donohoe T.J., Moore P.R., Beddoes R.L. J. Chem. Soc., Perkin Trans. 1. 1997;43-51. and references therein.
28. Niwa T., Tsuruoka T., Goi H., Kodama Y., Itoh J., Inouye S., Yamada Y., Niida T., Nobe M., Ogawa Y. J. Antibiot. 37:1984;1579-1586.
29. Altenbach H.-J., Himmeldirk K. Tetrahedron: Asymmetry. 6:1995;1077-1080.
30. Fleet G.W.J., Ramsden N.G., Witty D.R. Tetrahedron. 45:1989;327-336.