The combined use of stereoelectronic control and ring closing metathesis for the synthesis of (-)-8-epi-swainsonine

A novel and efficient synthesis of (-)-8-epi-swainsonine 2 is reported. Stereocontrolled diol formation from the bicyclic alkene 3 followed by a stereoselective vinylation of the aldehyde and ring closing metathesis gave the indolizidine ring system, which was converted into (-)-8-epi-swainsonine 2. © 2007 Elsevier Ltd. All rights reserved.