USE OF ATOM-TRANSFER RADICAL CYCLIZATIONS AS AN EFFICIENT ENTRY INTO A NEW "SEROTONERGIC" AZANORADAMANTANE

Article abstract of DOI:10.1016/S0040-4039(00)60166-1

A route to azanoradamantanes is described which makes use of an atom-transfer radical cyclization to afford 3-azabicyclo<3.3.0>ocatanes 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. Key words: Azanoradamantane; 3-azabicyclo<3.3.0>octane; serotonin