Use of atom-transfer radical cyclizations as an efficient entry into a new serotonergic azanoradamantane

Abstract A route to azanoradamantanes is described which makes use of an atom-transfer radical cyclization to afford 3-azabicyclo[3.3.0]octanes 3A and 3B . Subsequent elaboration of exo-allylamine functionality, followed by cyclization of the endo-hydroxymethyl intermediate 9 , affords the new azanoradamantanes 11 and 4 . This new azatricyclic system is useful for producing serotonin 5-HT3 antagonists and 5-HT4 agonists.