Total Synthesis of Rucaparib

Jinjae Park, Cheol Hong Cheon

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)4813-4817
Number of pages5
JournalJournal of Organic Chemistry
Volume87
Issue number7
DOIs
Publication statusPublished - 2022 Apr 1

Bibliographical note

Funding Information:
This work was supported by the National Research Foundation of Korea (NRF) grants funded by the Korean Government (NRF-2021R1A2C1012984 and NRF-2021R1A5A6002803 (Center for New Directions in Organic Synthesis)).

Publisher Copyright:
© 2022 American Chemical Society.

ASJC Scopus subject areas

  • Organic Chemistry

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