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 language | English |
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Pages (from-to) | 16782-16786 |
Number of pages | 5 |
Journal | Chemistry - A European Journal |
Volume | 23 |
Issue number | 66 |
DOIs | |
Publication status | Published - 27 Nov 2017 |
Externally published | Yes |
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