Hayashi Noriyuki, Miura Yusuke, Yokoshima Satoshi, Fukuyama Tohru
Graduate School of Pharmaceutical Sciences, University of Tokyo.
Graduate School of Pharmaceutical Sciences, Nagoya University.
Chem Pharm Bull (Tokyo). 2019 Jan 1;67(1):64-70. doi: 10.1248/cpb.c18-00718. Epub 2018 Oct 31.
An alternative synthetic route toward a key intermediate in the total synthesis of isoschizogamine is described. The Claisen-Johnson rearrangement stereoselectively constructed a quaternary carbon. Trifluoroperacetic acid mediated the Baeyer-Villiger oxidation to form a bicyclic lactone. The Mukaiyama-Matsuo protocol converted the lactone into an α,β-unsaturated lactone, that was used as the substrate for the rhodium-mediated 1,4-addition of an arylboronic acid.
描述了一条合成异裂环番木鳖碱全合成关键中间体的替代合成路线。克莱森-约翰逊重排反应立体选择性地构建了一个季碳。三氟过氧乙酸介导了拜耳-维利格氧化反应以形成一个双环内酯。向山-松尾反应将该内酯转化为α,β-不饱和内酯,该不饱和内酯用作铑介导的芳基硼酸1,4-加成反应的底物。