Cyclopropane ring-opening of tricyclo[3.3.0.02,8]octan-3-ones: a quick access to bicyclo[3.2.1]octanones from 2-methoxyphenols

We herein report an efficient and rapid strategy for the synthesis of highly functionalized bicyclo[3.2.1]octanones via sequential reactions: Diels–Alder reaction of MOB—ODPM rearrangement—reductive cleavage of cyclopropane, and its application to synthesize the core structure of drechslerine D.

Graphical abstractWe herein report an efficient and rapid strategy for the synthesis of highly functionalized bicyclo[3.2.1]octanones by sequential ‘Diels–Alder reaction of MOB–ODPM rearrangement—reductive cleavage of cyclopropane’ and its application for the synthesis of core structure of drechslerine D.Figure optionsDownload full-size imageDownload as PowerPoint slide