Synthesis of 3- and 5-endo-(6-Chloro-3-pyridoxy)-methyl-2-azabicyclo[2.2.0]hexane and 3-endo-(6-Chloro-3-pyridoxy)-methyl-2-azabicyclo[2.2.0]hex-5-ene. ABT-594 Analogs

Stereoselective photochemical ring closure of a 2-hydroxymethyl-1,2-dihydropyridine has been utilized for the syntheses of 3-endo-(6-Cl-3-pyridoxy)-methyl-2-azabicyclo[2.2.0]hex-5-ene and hexane analogs of the nicotinic acetylcholine receptor agonist ABT-594. The photochemical ring closure of a 4-hydroxymethyl-1,2-dihydropyridine has been utilized in the preparation of 5-endo-(6-chloro-3-pyridoxy)-methyl-2-azabicyclo[2.2.0]hexane.