Development of novel synthetic reactions based on release of strain energy in small ring system and its application to total syntheses of natural products

点击翻译按钮获取中文摘要

A small ring system such as cyclopropane ring and cyclobutane ring is one of the important functional groups to easily ring-open due to their ring strain release in organic synthetic chemistry.The reaction of alfa-pyrone derivatives which have an electron-withdrawing group at the 3-position with dimethylsulfoxonium methylide was examined. Bicycle[3.1.0]hexane derivatives and cyclopentadihydrofuran derivatives were selectively obtained on the basis of difference between substituent groups on the 5-position of alfa-pyrone. Furthermore, a natural product, adunctin B, was synthesized via a key reaction of coumarin which has an electron-withdrawing group at the 3-position with dimethylsulfoxonium methylide.