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Use Of Atom-Transfer Radical Cyclizations As An Efficient Entry Into A New Serotonergic Norazaadamantane, Daniel Flynn, Daniel Becker, Roger Nosal, Daniel Zabrowksi
Use Of Atom-Transfer Radical Cyclizations As An Efficient Entry Into A New Serotonergic Norazaadamantane, Daniel Flynn, Daniel Becker, Roger Nosal, Daniel Zabrowksi
Daniel P. Becker
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.