Synthetic study on indolic enamides

Tetrahedron

Volumn 59, Issue 47, 2003, Pages 9447-9454

  Kuramochi, Kouji ^a   Osada, Yuko ^a   Kitahara, Takeshi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Acylation; Curtius rearrangement; Indolic enamides

Indexed keywords

2 TRIMETHYLSILYLETHYL N [2 [[(2 TRIMETHYLSILYLETHOXY)CARBONYL] 6 BROMOINDOL 1 YL]ETHENYL]CARBAMATE; 2 TRIMETHYLSILYLETHYL N [2 [[(2 TRIMETHYLSILYLETHOXY)CARBONYL] 6 BROMOINDOLE] 3 ETHENYL]CARBAMATE; 2 TRIMETHYLSILYLETHYL N [2 [[(2 TRIMETHYLSILYLETHOXY)CARBONYL]INDOL 1 YL]ETHENYL]CARBAMATE; 2 TRIMETHYLSILYLETHYL N [2 [[(2 TRIMETHYLSILYLETHOXY)CARBONYL]INDOLYL] 3 ETHENYL]CARBAMATE; 3 [1 [(2 TRIMETHYLSILYLETHOXY)CARBONYL] 6 BROMOINDOLE]ACRYLIC ACID; 3 [1 [(2 TRIMETHYLSILYLETHOXY)CARBONYL]INDOLE]ACRYLIC ACID; ALKENYL GROUP; CHONDIAMIDE C; CHONDRIAMIDE A; COSCINAMIDE A; COSCINAMIDE B; IGZAMIDE; INDOLE DERIVATIVE; N [(2 TRIMETHYLSILYLETHOXY)CARBONYL] 6 BROMOINDOLE 3 CARBALDEHYDE; N [(2 TRIMETHYLSILYLETHOXY)CARBONYL]INDOLE 3 CARBALDEHYDE; N [[1 [(2 TRIMETHYLSILYL)ETHOXYCARBONYL] 6 BROMOINDOLE] 3 ETHENYL] ALPHA METHOXYOXOACETAMIDE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CHEMICAL PROCEDURES; DRUG SYNTHESIS; METHODOLOGY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0142153344     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.09.011     Document Type: Article

References (29)

1. Bokesch H.R., Pannell L.K., McKee T.C., Boyd M.R. Tetrahedron Lett. 41:2000;6305.
2. (a) Palermo J.A., Flower P.B., Seldes A.M. Tetrahedron Lett. 33:1992;3097
3. (b) Davyt D., Entz W., Fernandez R., Mariezcurrena R., Mombru A.W., Saldana J., Dominguez L., Coll J., Manta E. J. Nat. Prod. 61:1998;1560.
4. Dumdei E., Andersen R.J. J. Nat. Prod. 56:1993;792.
5. Len G.R. Synthesis. 1978;489.
6. Brossi A., Dolan L.A., Teitel S. Org. Synth. 56:1977;3.
7. (a) Ben-Ishai D., Gigee R. Tetrahedron Lett. 1965;4523
8. (b) Smith M.B., Wang C.-J., Keusenkothen P.F., Dembofsky B.T., Fay J.G., Zezza C.A., Kwon T.W., Sheu J., Son Y.C., Menezens R.F. Chem. Lett. 1992;247.
9. Rosenkranz G., Mancera O., Sondheimer F., Djerassi C. J. Org. Chem. 21:1956;520.
10. Still J.K., Becker Y. J. Org. Chem. 45:1980;2139.
11. (a) Ziegenbein W., Franke W. Chem. Ber. 90:1957;2291
12. (b) Hosokawa T., Takano M., Kuronki Y., Murahashi S.-I. Tetahahedron Lett. 33:1992;6643.
13. Brettle R., Mosedal A.J. J. Chem. Soc., Perkin Trans. 1. 1988;2185.
14. Kuramochi K., Watanabe H., Kitahara T. Synlett. 2000;397.
15. (a) Snider B.B., Song F. Org. Lett. 2:2000;407
16. Stefanuti I., Smith S.A., Taylor R.J.K. Tetrahedron Lett. 41:2000;3735
17. (b) Stefanuti I., Smith S.A., Taylor R.J.K. Tetrahedron Lett. 41:2000;3735
18. (a) Wu Y., Esser L., De Brabander J.K. Angew. Chem., Int. Ed. Engl. 39:2000;4308
19. (b) Wu Y., Seguil O.R., De Brabander J.K. Org. Lett. 2:2000;4241
20. (c) Bhattacharjee A., Seguil O.R., De Brabander J.K. Tetrahedron Lett. 42:2001;1217
21. (d) Snider B.B., Song F. Org. Lett. 3:2001;1817.
22. Kuramochi K., Osada Y., Kitahara T. Chem. Lett. 2002;128.
23. Smith A.B. III, Zheng J. Synlett. 2001;1019.
24. Feutrill J.T., Lilly M.J., Rizzacasa M.A. Org. Lett. 4:2002;525.
25. Roush W.R., Blizzard T.A. J. Org. Chem. 49:1984;4332.
26. Moffatt J.S. J. Chem. Soc. 1957;1442.
27. (a) Weinstock J. J. Org. Chem. 26:1961;3511.
28. (b) Kraiser C., Weinstock J. Org. Synth. 51:1971;48.
29. Faul M.M., Winneroski L.L., Krumrich C.A. J. Org. Chem. 63:1998;6053.