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

2007; American Chemical Society; Volume: 72; Issue: 19 Linguagem: Inglês

10.1021/jo0710883

1520-6904

Qi Liu, Evandro Maia Ferreira, Brian M. Stoltz,

Traditional and Medicinal Uses of Annonaceae

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.