An Oxidative Dearomatization Approach To Prepare the Pentacyclic Core of Ryanodol

2018-06-13T13:55:44Z (GMT) by Chen Xu Arthur Han Sarah E. Reisman
An approach to synthesize the pentacyclic framework of the polyol diterpenoid ryanodol is reported. The ABC tricycle was constructed by a Co-mediated Pauson–Khand reaction, and both radical and anionic cyclization pathways were developed to form the E-ring. In addition, a reaction sequence involving SeO<sub>2</sub>-mediated enone oxidation and hydroxyl-directed oxy-Michael addition was developed to introduce the A-ring oxidation. The feasibility of forming the bridging D-ring by an oxidative dearomatization was established.