Rapid stereoselective access to the tetracyclic core of puupehenone and related sponge metabolites using metal-free radical cyclisations of cyclohexenyl-substituted 3-bromochroman-4-ones

Abstract

The tetracyclic nucleus of puupehenone, 15-oxopuupehenol and other sesquiterpene–phenol natural products can be assembled stereoselectively in three steps, the last of these being the 6- endo- trig cyclisation of an alpha-keto radical generated from a substituted 2-(2-cyclohexenyl)ethyl 3-bromo-4-chromanone under metal-free conditions.