Total Synthesis of Rucaparib br
- Authors
- Park, Jinjae; Cheon, Cheol-Hong
- Issue Date
- 1-4월-2022
- Publisher
- AMER CHEMICAL SOC
- Citation
- JOURNAL OF ORGANIC CHEMISTRY, v.87, no.7, pp.4813 - 4817
- Indexed
- SCIE
SCOPUS
- Journal Title
- JOURNAL OF ORGANIC CHEMISTRY
- Volume
- 87
- Number
- 7
- Start Page
- 4813
- End Page
- 4817
- URI
- https://scholar.korea.ac.kr/handle/2021.sw.korea/141848
- DOI
- 10.1021/acs.joc.2c00083
- ISSN
- 0022-3263
- Abstract
- A concise total synthesis of rucaparib, an FDA-approved drug for ovarian and prostate cancers, is reported. TheHeck reaction of the commercially available aryl iodide withacrylonitrile provided the desired (E)-2-aminocinnamonitrile deriva-tive. A subsequent imino-Stetter reaction of the aldimine derived from2-aminocinnamonitrile and aldehyde furnished indole-3-acetonitrilebearing the desired substituents at appropriate positions. Theconstruction of thefinal azepinone scaffold via reduction of thenitrile group followed by seven-membered lactamization affordedrucaparib. Notably, the synthesis of rucaparib is achieved usingcommercially available starting materials in only three separationoperations with 54% overall yield.
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