Stereoselective synthesis of (-)-8-epi-swainsonine starting with a chiral aziridine

Abstract

An efficient synthesis of (-)-8-epi-swainsonine, starting from a commercially available 1-(R)-alpha-methylbenzylaziridine-2-methanol, was developed. The synthetic route utilizes stereocontrolled Sharpless asymmetric dihydroxylation governed by AD-mix-beta followed by an aziridine ring opening-cyclization sequence to generate the five membered N-heterocyclic ring system present in the bicyclic target. A subsequent stereoselective allylation and piperidine ring forming cyclization then produced a precursor that was converted into (-)-8-epi-swainsonine. (c) 2012 Elsevier Ltd. All rights reserved.