New palladium-catalyzed reaction pathway to the Erythrina skeleton

Journal of Organic Chemistry

Volumn 71, Issue 5, 2006, Pages 2185-2187

  Kim, Guncheol ^a   Kim, Jin Hee ^a   Lee, Ki Youn ^a  

^a Chungnam National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

KETOESTERS; PALLADIUM-CATALYZED ARYLATION;

AMINES; CATALYSIS; CONDENSATION; RATE CONSTANTS;

PALLADIUM;

13 DEMETHOXYERYTHRATIDINONE; ALKALOID; BETA ERYTHROIDINE; ERYSOTRAMIDINE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CATALYSIS; CYCLIZATION; DRUG STRUCTURE; ERYTHRINA; HECK REACTION; REACTION ANALYSIS; SUBSTITUTION REACTION;

ALKALOIDS; AMINES; CATALYSIS; CYCLIZATION; ERYTHRINA; ESTERS; KETONES; LACTAMS; MOLECULAR CONFORMATION; PALLADIUM;

EID: 33644641630     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052500m     Document Type: Article

References (15)

1. (a) Tanaka, H.; Tanaka, T.; Etoh, H.; Goto, S.; Terada, Y. Heterocycles 1999, 51, 2759-2764.
2. (b) Dyke, S. F.; Quessy, S. N. The Alkaloids; Rodrigo, R. G. A., Ed.; Academic Press: New York, 1981; Vol. 18.
3. (a) Miranda, L. D.; Zard, S. Z. Org. Lett. 2002, 4, 1135-1138.
4. (b) Chikaoka, S.; Toyao, A.; Ogasawara, M.; Tamura, O.; Ishibashi H. J. Org. Chem. 2003, 68, 312-318 and references therein.
5. (a) Allin, S. M.; Streetley, G. B.; Slater, M.; James, S. L.; Martin, W. P. Tetrahedron Lett. 2004, 45, 5493-5496.
6. (b) Allin, S. M.; James, S. L.; Elsegood, M. R. J.; Martin, W. P. J. Org. Chem. 2002, 67, 9464-9467.
7. (c) Padwa, A.; Lee, H. I.; Rashatasakhon, P.; Rose, M. J. Org. Chem. 2004, 69, 8209-8218 and references therein,
8. (d) Katritzky, R. A.; He, H.-Y.; Jiang, R. Tetrahedron Lett. 2002, 43, 2831-2833.
9. (a) Rigby, J. H.; Hughes, R. C.; Heeg, M. J. J. Am. Chem. Soc. 1995, 117, 7834-7835.
10. (b) Rigby, J. H.; Deur, C.; Heeg, M. J. Tetrahedron Lett. 1999, 40, 6887-6890.
11. Dréau, M.-A.; Desmaële, D.; Dumas, F.; d'Angelo, J. J. Org. Chem. 1993, 58, 2933-2935.
12. For reviews on palladium-catalyzed α-arylation of carbonyl compounds, see: (a) Lloyd-Jones, G. C. Angew. Chem., Int. Ed. 2002, 41, 953-955.
13. (b) Culkin, D. A.; Hartwig, J. F. Acc. Chem. Res. 2003, 36, 234-245.
14. Culkin, D. A.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 5816-5817.
15. Ishibashi, H.; Sato, T.; Takahashi, M.; Hayashi, M.; Ikeda, M. Heterocycles 1988, 27, 2787-2790.