Total synthesis of amorfrutin B via a Pd-catalyzed regioselective geranyl migration-decarboxylation-cycloaromatization cascade

Abstract

A biomimetic total synthesis of amorfrutin B, a resorcylate with geranyl bibenzyl scaffold, has been completed in eight steps from 2,2,6-trimethyl-4H-1,3-dioxin-4-one. The key step utilized a highly regioselective Pd-catalyzed geranyl migration-decarboxylation-cycloaromatization cascade. The methodology should be of practical utility in the construction of geranyl bibenzyl scaffolds manifested in many natural products.