当前位置: X-MOL 学术Org. Process Res. Dev. › 论文详情
Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)
Efficient and Scalable Asymmetric Total Synthesis of (−)-Emetine with Pharmaceutical Grade Quality; First Multigram Scale Synthesis
Organic Process Research & Development ( IF 3.4 ) Pub Date : 2023-01-24 , DOI: 10.1021/acs.oprd.2c00355
Masatoshi Yamada 1 , Kazuki Azuma 1 , Iori Takizawa 1 , Yuki Ejima 1 , Mitsuhisa Yamano 1 , Kimio Satoh 2 , Takayuki Doi 3 , Hirofumi Ueda 3 , Hidetoshi Tokuyama 3
Affiliation  

A scalable asymmetric total synthesis of (−)-emetine, a natural product alkaloid from ipecac species and one of the main active ingredients in ipecac syrup used in emetics, has been accomplished. The synthetic route featured a total of 13 steps of highly efficient chemical reactions, including catalytic asymmetric allylation and an industrial deoxygenation of an aliphatic compound, which obviated the need for any chromatographic purification. (−)-Emetine·2HCl was obtained in 12% overall yield and over 93.2% HPLC purity. The synthesis was easily scaled up to 237.1 g and should be amenable to the production of larger quantities for ongoing drug development, while the compound is currently provided as natural ipecac syrup for a clinical use.

中文翻译:

(−)-Emetine 的高效且可扩展的不对称全合成,具有医药级品质;第一次多字母表合成

(−)-emetine 的可扩展不对称全合成已经完成,emetine 是一种来自吐根物种的天然产物生物碱,也是催吐剂中使用的吐根糖浆中的主要活性成分之一。该合成路线共有 13 个高效化学反应步骤,包括催化不对称烯丙基化和脂肪族化合物的工业脱氧,无需任何色谱纯化。(−)-Emetine·2HCl 以 12% 的总收率和超过 93.2% 的 HPLC 纯度获得。该合成很容易放大到 237.1 克,应该可以为正在进行的药物开发生产更大数量的化合物,而该化合物目前以天然吐根糖浆的形式提供用于临床。
更新日期:2023-01-24
down
wechat
bug