Liron Frédéric, Fontana Francesco, Zirimwabagabo Jean-Olivier, Prestat Guillaume, Rajabi Jamshid, La Rosa Concetta, Poli Giovanni
Institut Parisien de Chimie Moléculaire UMR CNRS 7201, FR2769 Institut de Chimie Moléculaire, UPMC Univ Paris 06, Place Jussieu, 75005, Boite 183, Paris, France.
Org Lett. 2009 Oct 1;11(19):4378-81. doi: 10.1021/ol9017326.
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.
从芝麻酚出发，经六步反应以55%的产率立体选择性地合成了卡帕酮。合成序列的关键步骤是通过铃木-宫浦交叉偶联反应直接引入丙烯基侧链。随后的钯（II）催化氧化偶联反应生成卡帕酮，作为单一非对映异构体，与起始前体的几何构型无关。为此转化提出了一种新机制。
