An Oxidative Dearomatization Approach To Prepare the Pentacyclic Core of Ryanodol

作者:Xu Chen*; Han Arthur; Reisman Sarah E*
来源:Organic Letters, 2018, 20(13): 3793-3796.
DOI:10.1021/acs.orglett.8b01387

摘要

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 SeO2-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.

  • 出版日期2018-7-6