Synthesis of bicyclic carbamates as precursors of Sedum alkaloid derivatives

Tetrahedron

Volumn 61, Issue 6, 2005, Pages 1595-1602

  Szakonyi, Zsolt ^a,b   D'Hooghe, Matthias ^a   Kanizsai, Iván ^a,b   Fülöp, Ferenc ^b   De Kimpe, Norbert ^a  

^a GHENT UNIVERSITY   (Belgium)

^b UNIVERSITY OF SZEGED   (Hungary)

Author keywords

Bicyclic carbamate; Enamide; Sedum alkaloid; Stereoselectivity

Indexed keywords

ALDEHYDE; ALKALOID DERIVATIVE; CARBAMIC ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; KETONE DERIVATIVE; PHOSPHINE OXIDE DERIVATIVE; SEDUM ALKALOID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CYCLIZATION; DRUG SYNTHESIS; OLEFINATION; PRIORITY JOURNAL; QUANTUM YIELD; REDUCTION KINETICS; RING OPENING; STEREOCHEMISTRY;

SEDUM;

EID: 12344261691     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.08.073     Document Type: Article

References (25)

1. Elbein, A. D.; Molyneux, R. Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley: New York, 1987; Vol. 57, p 1.
2. D. O'Hagen Nat. Prod. Rep. 14 1997 637
3. R.W. Bates, and K. Sa-Ei Tetrahedron 58 2002 5957 5978 and references cited therein
4. R. Stragies, and S. Blechert Tetrahedron 55 1999 8179 8188
5. T. Kochi, T.P. Tang, and J.A. Ellman J. Am. Chem. Soc. 125 2003 11276 11282
6. G.M. Strunz, and J.A. Findlay Pyridine and Piperidine Alkaloids A. Brossi The Alkaloids Vol. 26 1985 Academic New York 89 174
7. J.H. Kim, H. 't Hart, and J.F. Stevens Phytochemistry 41 1996 1319 1324
8. H. Takahata, M. Kubota, and T. Momose Tetrahedron Lett. 38 1997 3451 3454
9. Meth-Cohn, O.; Yu, C.-Y.; Lestage, P.; Lebrun, M.-C.; Cagniard, D.-H.; Renard, P., Eur. Pat., 2000, EP 1050531 A1, 08/11/2000; Chem. Abstr. 2000, 133, 350144.
10. M.F. Roberts, B.T. Cromwell, and D.E. Webster Phytochemistry 6 1967 711 717
11. E. Schuster, C. Hesse, and D. Schumann Synlett 1991 916 918
12. H. De Koning, G.N. Mallo, A. Springer-Fidder, K.E.C. Subramanian-Erhart, and H.O. Huisma Recl. Trav. Chim. Pays-Bas 92 1973 683 688
13. N. De Kimpe, and C. Stevens J. Org. Chem. 58 1993 2904 2906
14. R.C. Miller J. Chem. Soc., Perkin Trans. 1 1959 2013 2015
15. A. Couture, E. Deniau, P. Grandclaudon, S. Lebrun, S. Léonce, P. Renard, and B. Pfeiffer Bioorg. Med. Chem. 8 2000 2113 2125
16. S.V. Ley, B. Lygo, H.M. Organ, and A. Wonnacott Tetrahedron 41 1985 3825 3836
17. S. Lebrun, A. Couture, E. Deniau, and P. Grandclaudon Tetrahedron 55 1999 2659 2670
18. P.L. McGrane, M. Jensen, and T. Livinghouse J. Am. Chem. Soc. 114 1992 5459 5460
19. A.I. Meyers, P.D. Edwards, T.R. Bailey, and G.E. Jagdmann J. Org. Chem. 50 1985 1019 1026
20. C. Agami, and F. Couty Tetrahedron 58 2002 2701 2724 and references cited therein
21. S. Brocherieux-Lanoy, H. Dhimane, J.-C. Poupon, C. Vanucci, and G. Lhommet J. Chem. Soc., Perkin Trans. 1 1997 2163 2165
22. E. Kaiser Sr., J.P. Tam, T.M. Kubiak, and R.B. Merrifield Tetrahedron Lett. 29 1988 303 306
23. H. Takahata, M. Kubota, and N. Ikota J. Org. Chem. 64 1999 8594 8601
24. J.F. Stevens, H. 't Hart, H. Hendriks, and T.M. Malingré Phytochemistry 31 1992 3917 3924
25. M.J. Schneider, S. Brendze, and J.A. Montali Phytochemistry 39 1995 1387 1390