摘要
A short formal stereoselective synthesis of （-）-swainsonine （1） is described. Our synthesis started with the versatile building block （R）-3-benzyloxyglutarimide 5. Through controlled regioselective reduction, Ley＇s-sulfone chemistry （N-α-sulfonylation and ZnCl2-catalyzed N-α-amidovinylation）, an RCM reaction, and an amide reduction, the synthesis of unsaturated indolizidine （8R,8aS）-3 has been achieved in five steps. The indolizidine （8R,8aS）-3 is an advanced intermediate toward the synthesis of （-）-swainsonine （1）.
A short formal stereoselective synthesis of （-）-swainsonine （1） is described. Our synthesis started with the versatile building block （R）-3-benzyloxyglutarimide 5. Through controlled regioselective reduction, Ley＇s-sulfone chemistry （N-α-sulfonylation and ZnCl2-catalyzed N-α-amidovinylation）, an RCM reaction, and an amide reduction, the synthesis of unsaturated indolizidine （8R,8aS）-3 has been achieved in five steps. The indolizidine （8R,8aS）-3 is an advanced intermediate toward the synthesis of （-）-swainsonine （1）.
基金
financial support from the National Basic Research Program(973 Program)of China(No. 2010CB833200)
the NSF of China(Nos.21332007,21072160)
the Program for Changjiang Scholars and Innovative Research Team in University(PCSIRT)of Ministry of Education,China for financial support
