Absolute Stereochemistry of (-)-Preorixine and Related Compounds

Abstract

The absolute stereochemistry of the C-2' position of (-)-preorixine, postulated to be an important biosynthetic precursor of various quinoline alkaloids, was assigned as R by the combination of its chemical transformation and the extended Mosher method. The stereochemistry of the C-2' position of (+)-orixine was also concluded to be R, establishing taht no inversion occurred when (-)-preorixine was transformed into (+)-orixine.