An arene-alkene photocycloaddition-radical cyclization cascade: The first synthesis of cis,cis,cis,trans-[5.5.5.5]-fenestranes

Abstract

The first cis,cis,cis,trans-[5.5.5.5]-fenestranes have been synthesized in three steps using a novel arene-alkene photocycloaddition-radical cyclization cascade, which creates overall 5 new rings and 8 stereogenic centers. A lead tetraacetate mediated ring expansion of a 5,5-fused ring system, discovered in the course of exploring the chemistry of these new materials, is also described.