Enantioselective Synthesis of Swainsonine, a Trihydroxylated Indolizidine Alkaloid

Article abstract of DOI:10.1021/jo00203a039

A total synthesis of (-)-swainsonine in 21 steps and 6.6percent overall yield starting from trans-1,4-dichloro-2-butene and N-benzyl-p-toluenesulfonamide is described.The synthesis employs the methodology of the Masamune/Sharpless approach to polyhydroxylated natural products.