title: Total synthesis of (S)-14-azacamptothecin.
abstract: A concise synthesis of (S)-14-azacamptothecin has been accomplished in 8 steps from commercially available (R)-2-hydroxybutanoic acid. The key strategy involved in this synthesis is the Michael addition/β-elimination sequence to construct the chiral quaternary carbon center, followed by palladium catalyzed cyanation and formal [4 + 2] cycloaddition/elimination/aromatization in a one pot manner to form the pyrrolopyrimidin-4-one moiety.
authors.affiliation: Jiangsu Key Laboratory of Translational Research and Therapy for Neuro-Psycho-Diseases and College of Pharmaceutical Sciences, Soochow University, Suzhou, Jiangsu 215123, P. R. China. fliu2@suda.edu.cn.
authors.forename: Feng
authors.initials: F
authors.lastname: Liu
authors.forename: Chaozhong
authors.initials: C
authors.lastname: Li
mesh_terms: D002166:Camptothecin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: C499708:14-azacamptothecin; D002166:Camptothecin