A Short, Enantioselective Synthesis of (-)-Swainsonine

Article abstract of DOI:10.1021/ja00189a034

A practical, enantioselective synthesis of (-)-swainsonine (1) has been achieved in seven steps from 2,3-O-isopropylidene-D-erythorose (6).The key step involves the construction of the bicyclic imine 4 by an intramolecular 1,3 dipolar cycloaddition of azide 5.This study highlights the synthetic utility of the intramolecular 1,3 dipolar cycloaddition of the unactivated olefinic azides in natural product synthesis.