Use of Atom-transfer Radical Cyclizations as an Efficient Entry into a New Serotonergic Norazaadamantane
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.
Flynn, Daniel L.; Becker, Daniel; Nosal, Roger; and Zabrowksi, Daniel. Use of Atom-transfer Radical Cyclizations as an Efficient Entry into a New Serotonergic Norazaadamantane. Tetrahedron Letters, 33, 48: , 1992. Retrieved from Loyola eCommons, Chemistry: Faculty Publications and Other Works, http://dx.doi.org/10.1016/S0040-4039(00)60166-1
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© 1992 Elsevier