Synthesis of Spirocyclic Pyrrolidines: Advanced Building Blocks for Drug Discovery

Bohdan A. Chalyk, Maryna V. Butko, Oksana O. Yanshyna, Konstantin S. Gavrilenko, Tetiana V. Druzhenko, Pavel K. Mykhailiuk*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

51 Citations (Scopus)

Abstract

In the context of drug discovery, novel spirocyclic pyrrolidines have been synthesized in two steps from common three- to seven-membered-ring (hetero)alicyclic ketones. The key transformation is a reaction between an electron-deficient exocyclic alkene and an in situ generated N-benzyl azomethine ylide. The developed method has been used to synthesize the central diamine core of the known antibacterial agents Sitafloxacin and Olamufloxacin.

Original languageEnglish
Pages (from-to)16782-16786
Number of pages5
JournalChemistry - A European Journal
Volume23
Issue number66
DOIs
Publication statusPublished - 27 Nov 2017
Externally publishedYes

Funding

The authors are very grateful to Dr. S. Shishkina for performing X-ray studies, to Prof. A. Tolmachev for financial support, to Mrs. I. Sadkova for help with preparation of the manuscript, and to Dr. O. Brusylovets, V. Alekseev, and V. V. Skyba for performing chromatographic purifications. Dr. S. Nikitin is acknowledged for providing acid 25. All other chemicals were kindly provided by Enamine Ltd. (www.enamine.net).

All Science Journal Classification (ASJC) codes

  • Catalysis
  • General Chemistry
  • Organic Chemistry

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