Azaspirovesamicols-Regioselective Synthesis and Crystal Structure Analysis of a Novel Class of Vesamicol Analogues as Potential Ligands for the Vesicular Acetylcholine Transporter

This report describes the high regioselectivity of nucleophilic epoxide ring-opening reactions which resulted in two of four possible regioisomers of N-benzoyl- (5a and 5b) and N-fluorobenzoylazaspirovesamicol derivatives (6a and 6b), respectively. Based on structural information obtained from X-ray crystal structure analyses of 5a and 5b the mode of epoxide ring-opening is discussed