Palladium catalyzed C-N bond formation in the synthesis of 7-amino-substituted tetracyclines.
A facile synthesis of 7-alkylamino- and 7-cycloalkylaminotetracycline derivatives has been accomplished using an in situ generated aminostannane precursor. This procedure is advantageous in that it allows the concise synthesis of a number of unreported tetracycline derivatives that are cumbersome to prepare through traditional methods. These compounds are crucial to understanding structure activity relationships in the D-ring of tetracycline-type antibiotics and the acquired efflux resistance mechanism to this class of antibiotics.
Koza
Darrell J
DJ
Eastern Connecticut State University, Center for Antimicrobial Resistance, Goddard Hall, 83 Windham Street, Willimantic, Connecticut 06226, USA. kozad@easternct.edu
Nsiah
Yaw A
YA
D000588:Amines / Q000737:chemistry*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D002851:Chromatography, High Pressure Liquid; D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D013329:Structure-Activity Relationship; D013754:Tetracyclines
D000588:Amines; D000900:Anti-Bacterial Agents; D013754:Tetracyclines; D010165:Palladium; D002244:Carbon; D009584:Nitrogen