瑞波西汀关键中间体的合成(英文)

A Practical Synthesis of Key Chiral Intermediate for (S,S)-Reboxetine

瑞波西汀在抑郁症的短期和长期治疗中均表现出有效性和耐受性 ,而且 (S,S)型立体异构体的抗抑郁能力最高。作者研究了反式肉桂醇的不对称环氧化。在温和条件下 ,采用便宜的过氧化氢 ,在 D-果糖衍生物催化下得到了 (S,S)构型瑞波西汀关键中间体 (R,R)肉桂醇环氧化物 ,获得了高产率和立体选择性。

Reboxetine shows efficacy and tolerability in both short and long term treatment of depression , and the (S,S) enantiomer is the most potent. Asymmetric epoxidation of cinnamyl alcohol was studied. (R,R) Cinnamyl alcohol epoxide, a key intermediate of (S,S) reboxetine, was synthesized under mild conditions using inexpensive hydrogen peroxide as an oxidant catalyzed by D fructose derived ketone with high yield and excellent enantiomeric excess.