Pyridine analogs of (−)-cytisine and varenicline: cholinergic receptor probes

…, J Candler, CG Bashore, EP Arnold, BT O'Neill…

Index: Demers, Sebastien; Stevenson, Heather; Candler, John; Bashore, Crystal G.; Arnold, Eric P.; O'Neill, Brian T.; Coe, Jotham W. Tetrahedron Letters, 2008 , vol. 49, # 21 p. 3368 - 3371

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Citation Number: 15

Abstract

A series of bicyclic pyridine containing alkaloids related to (−)-cytisine and varenicline are described. Synthetic access via regioisomeric metalation of alkoxy-and halo-pyridines gains entry to all four isomeric [3.3. 1]-bicyclic targets. Regioselective and sequential oxidative cleavage of dicyclopentadiene generates a related [3.2. 1]-bicyclic analog.