Efficient construction of ABC-tricyclic core of schweinfurthins and its application in amide based analog synthesis

Abstract

To accelerate the medicinal chemistry efforts, an efficient and reliable synthesis of amide isosteres of Schweinfurthin G, where the central olefinic linkage between C and D rings has been replaced with amide bond, is described. The approach relied on a copper mediated coupling reaction of organo-magnesium species with allylic chloride is easily amenable to rapid analoging to generate amide based isosteres of the natural product.