Convergency and Divergency as Strategic Elements in Total Synthesis: The Total Synthesis of (-)-Drupacine and the Formal Total Synthesis of (±)-Cephalotaxine,(-)- …

Q Liu, EM Ferreira, BM Stoltz

Index: Liu, Qi; Ferreira, Eric M.; Stoltz, Brian M. Journal of Organic Chemistry, 2007 , vol. 72, # 19 p. 7352 - 7358

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Citation Number: 44

Abstract

A concise route toward the syntheses of (-)-drupacine and (+)-and (-)-cephalotaxine has been developed. The syntheses rely on Pd (II)-catalyzed aerobic oxidative heterocyclization chemistry, which was employed to rapidly construct an important spirocyclic amine intermediate. A dynamic β-elimination/conjugate addition process was strategically applied to complete the first asymmetric total synthesis of (-)-drupacine.