L-メチオニンを原料とするオセルタミビルのアジドフリー合成法

抄録

The recent emergence of world-shaking avian flu virus H5N1 has prompted many nations to stock Tamiflu^TM, the potent anti-influenza drug developed by Gilead Science. The present commercial production, however, relies heavily on the semisynthesis starting from shikimic acid of limited availability, which would hamper to stock a sufficient amount of Tamiflu. Given the current supply issue, we have started our program directed toward the synthesis of oseltamivir, the free base of Tamiflu. Recently we have succeeded in developing a synthetic route starting from L-methionine. The key features of the present method are: (1) ready availability of the starting material, (2) azide-free synthetic route, and (3) highly stereoselective construction of the three contiguous chiral centers by means of Staudinger reaction.