Palladium Catalyzed C−N Bond Formation in the Synthesis of 7-Amino-Substituted Tetracyclines

• Published in: Journal of organic chemistry Vol. 67; no. 14; pp. 5025 - 5027
• Main Authors: Koza, Darrell J, Nsiah, Yaw A
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 12.07.2002; Amer Chemical Soc
• Subjects: Alicyclic compounds; Alicyclic compounds, terpenoids, prostaglandins, steroids; Amines - chemistry; Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - chemistry; Carbon - chemistry; Catalysis; Chemistry; Chemistry, Organic; Chemistry, Organic - methods; Chromatography, High Pressure Liquid; Cyclization; Exact sciences and technology; Magnetic Resonance Spectroscopy; Molecular Structure; Nitrogen - chemistry; Organic chemistry; Palladium - chemistry; Physical Sciences; Preparations and properties; Science & Technology; Structure-Activity Relationship; Tetracyclines; AMINATION; 6-DEOXYTETRACYCLINES; Catalytic reaction; Transition element complexes; Tetracycline derivatives; Alcohol; Palladium complex; Tetracyclic compound; Ketone; Iodine Organic compounds; Amine; Carboxamide; Platinoid Complexes; Aromatic compound; Chemical synthesis; Organic stannane
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo0256585

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.