化学
腈
丙烯腈
醛
组合化学
吲哚试验
产量(工程)
芳基
碘化物
有机化学
烷基
催化作用
聚合物
材料科学
共聚物
冶金
作者
Jinjae Park,Cheol‐Hong Cheon
标识
DOI:10.1021/acs.joc.2c00083
摘要
A concise total synthesis of rucaparib, an FDA-approved drug for ovarian and prostate cancers, is reported. The Heck reaction of the commercially available aryl iodide with acrylonitrile provided the desired (E)-2-aminocinnamonitrile derivative. A subsequent imino-Stetter reaction of the aldimine derived from 2-aminocinnamonitrile and aldehyde furnished indole-3-acetonitrile bearing the desired substituents at appropriate positions. The construction of the final azepinone scaffold via reduction of the nitrile group followed by seven-membered lactamization afforded rucaparib. Notably, the synthesis of rucaparib is achieved using commercially available starting materials in only three separation operations with 54% overall yield.
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