Abstract
Carbohydrates have played an important role in organic synthesis. Since they contain
many stereocenters, they have been widely used as chiral-pool starting materials.
Herein, we report the asymmetric formal synthesis of (–)-swainsonine, which exhibits
anticancer and immunosuppressive activities and inhibits lysosomal α-mannosidase activity,
from d-mannose and d-arabinose. The synthesis utilized Zn-mediated Bernet–Vasella reaction, Horner–Wadsworth–Emmons
olefination, and Grubbs olefin metathesis as key reactions.
Key words
arabinose - mannose - swainsonine - natural product synthesis - anticancer
