置換基効果に基づく効率的エン－イン閉環メタセシス反応を利用する２－アルキルイソファゴミン類の合成研究

抄録

Molecular chemical chaperone is a small molecule that interacts with proteins to induce some changes in their forms and functions. Isofagomine is known to function as a molecular chemical chaperone of glycosidase and is expected as a new molecular therapy for glycosphingolipid storage disorders such as Gaucher disease. We focused our attentions on design of new isofagomine derivatives in order to develop more promising molecules. It is reported that introduction of an aliphatic chain into isofagomine changed reactivity and selectivity against glycosidase. Based on these results we designed 2-alkylisofagomines. In this study, we have developed a concise synthetic root to 2-alkylisofagomines using allylic hydroxy group accelerated ring-closing enyne metathesis as a key step. This root accomplished construction of 2-propylisofagomine. Details of the root are reported.