A New Cross-Coupling-Based Synthesis of Carpanone

作者:Liron Frederic; Fontana Francesco; Zirimwabagabo Jean Olivier; Prestat Guillaume; Rajabi Jamshid; La Rosa Concetta; Poli Giovanni*
来源:Organic Letters, 2009, 11(19): 4378-4381.
DOI:10.1021/ol9017326

摘要

Carpanone has been stereoselectively synthesized in 55% yield and six steps from sesamol. The key step of the synthetic sequence is the direct Introduction of the propenyl side chain via a Suzuki-Miyaura cross-coupling reaction. The subsequent Pd(II)-catalyzed oxidative coupling yields carpanone as a single diastereoisomer independently of the geometric configuration of the starting precursor. A new mechanism is proposed for this transformation.

  • 出版日期2009-10-1