154.Synthesis of Desacyl Furanmonogones A and B

Dian Li, Jinfeng Yang, Bingyan Liu, Jianxian Gong,* and Zhen Yang*

Org. Lett. 2021, 23(12), 4532–4537

A strategy for the stereoselective synthesis of desacyl furanmonogones A and B has been achieved. The key steps in this synthesis are (1) an Fe(ClO₄)₃-mediated oxidative radical cyclization for construction of a cis-fused [5–6]-bicyclic core with a bridged lactone substitute, (2) a phosphorane-mediated rearrangement to convert the cis-fused [5–6]-bicyclic core to the corresponding trans-fused [5–6]-bicyclic core, and (3) a Au-catalyzed cascade reaction for formation of the 4,5-seco-3(2H)-furanone motif.