A Short, Efficient, and Stereoselective Total Synthesis of a Pyrrolidine Alkaloid:  (−)-Codonopsinine

Abstract

An efficient total synthesis of antibiotic (-)-codonopsinine 1 with an overall yield of 44% was achieved from d-alanine as a chiral template. The key steps in our strategy are modified Sharpless asymmetric dihydroxylation reaction and the highly stereoselective intramolecular acid-catalyzed amidocyclization.