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Total synthesis of (S)-14-azacamptothecin
1Jiangsu 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.
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.
