Yamaoka Yousuke
Graduate School of Pharmaceutical Sciences, Kyoto University.
Yakugaku Zasshi. 2016;136(11):1517-1523. doi: 10.1248/yakushi.16-00202.
A potassium base-promoted formal [2+2] cycloaddition of 2-acyl-2'-vinyl-1,1'-biaryls was developed to afford benzo-fused polycyclic cyclobutanols in a highly stereoselective manner. We demonstrated synthesis of substituted polycyclic aromatic hydrocarbons and these heterocyclic derivatives via this cyclization, followed by an acid-promoted rearrangement. Furthermore, asymmetric total synthesis of phenanthroindolizidine alkaloid (-)-tylophorine was achieved using our methodology and late-stage asymmetric hydrogenation of a cyclic imine.
开发了一种钾碱促进的2-酰基-2'-乙烯基-1,1'-联芳基的形式[2+2]环加成反应，以高立体选择性的方式得到苯并稠合的多环环丁醇。我们展示了通过这种环化反应，随后进行酸促进的重排反应，合成取代的多环芳烃和这些杂环衍生物。此外，使用我们的方法和环状亚胺的后期不对称氢化反应，实现了菲并吲哚里西啶生物碱（-）- tylophorine的不对称全合成。
