Tropane and related alkaloid skeletons via a radical [3+3]-annulation process

Abstract

N-arylated bicyclic alkaloid skeletons are attractive scaffolds for medicinal chemistry, but aren’t conveniently accessible via the classical Robinson tropane synthesis. Here, a mild and simple visible-light catalyzed radical [3 + 3]-annulation process is designed, affording N-arylated 8-azabicyclo[3.2.1]octane and 9-azabicyclo[3.3.1]nonane derivatives with good yields and high diastereoselectivity from readily available starting materials.