Palladium-catalyzed cross-coupling in the synthesis of pyridinyl boxazomycin C analogues

Journal of Organic Chemistry

Volumn 70, Issue 18, 2005, Pages 7436-7438

  Richardson, Chris ^a   Rewcastle, Gordon W ^a   Hoyer, Denton ^b   Denny, William A ^a  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

^b PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; PALLADIUM; SYNTHESIS (CHEMICAL);

2-THIOMETHYLBENZOXAZOLES; PALLADIUM-CATALYZED CROSS-COUPLINGS; PYRIDINYL BOXAZOMYCIN C ANALOGUES;

ORGANIC COMPOUNDS;

2 THIOMETHYLBENZOXAZOLE; BENZOXAZOLE DERIVATIVE; BOXAZOMYCIN C DERIVATIVE; PALLADIUM; PYRIDINE DERIVATIVE; STANNYLPYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHROMATOGRAPHY; CROSS COUPLING REACTION; DEPROTECTION REACTION; LOW TEMPERATURE PROCEDURES; ORGANIC CHEMISTRY; SYNTHESIS;

ANTI-BACTERIAL AGENTS; BENZOXAZOLES; CATALYSIS; PALLADIUM; PYRIMIDINES;

EID: 24144490376     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0510033     Document Type: Article

References (14)

1. Kusumi, T.; Ooi, T.; Walchi, M. R.; Kakisawa, H. J. Am. Chem. Soc. 1988, 110, 2954-2958.
2. Suto, M. J.; Turner, W. R. Tetrahedron Lett. 1995, 36, 7213-7216.
3. Li, J. J.; Gribble, G. W. Palladium in Heterocyclic Chemistry: A Guide for the Synthetic Chemist; Pergamon: Amsterdam, 2000.
4. Hodgetts, K. J.; Kershaw, M. T. Org. Lett. 2002, 4, 2905-2907.
5. Kelly, T. R.; Lang, F. J. Org. Chem. 1996, 61, 4623-4633.
6. For example, Suto and Turner used LiI in refluxing pyridine to deprotect the aryl methyl ether; see ref 2.
7. Angyal, S. J.; Bullock, E.; Hanger, W. G.; Howell, W. C.; Johnson, A. W. J. Chem. Soc. 1957, 1592-1602.
8. Nachman, R. J. J. Heterocycl. Chem. 1982, 19, 1545-1547.
9. Langille, N. F.; Dakin, L. A.; Panek, J. S. Org. Lett. 2002, 4, 2485-2488.
10. Chen, W.-B.; Jin, G.-Y. Heteroat. Chem. 2001, 12, 151-155.
11. Goldstein, S. W.; Dambek, P. J. J. Heterocycl. Chem. 1990, 27, 335-336.
12. Egi, M.; Lebeskind, L. S. Org. Lett. 2003, 5, 801-802.
13. Alphonse, F.-A.; Suzenet, F.; Keromnes, A.; Lebret, B.; Guillaumet, G. Org. Lett. 2003, 5, 803-805.
14. Egi and Lebeskind advocate the use of copper(I) 3-methylsalicylate (CuMeSal); see ref 12.