Abstract
(3S,4R)-3-(1'(R)-tert-Butyldimethylsilyloxyethyl)-4-chloro-2-azetidinone (2), a potent intermediate for the synthesis of carbapenem antibiotics, was synthesized by thermal ring opening/acylation of (3S,5R,6S)-6-(1'(R)-tert-butyldimethylsilyloxyethyl)penicillanate S-oxide (8) leading to 4-acylthio-2-azetidinone derivative 9 and subsequent removal of the N-substituent followed by electrooxidative desulfurization/chlorination of the C(4)-acylthio moiety.
| Original language | English |
|---|---|
| Pages (from-to) | 1471-1484 |
| Number of pages | 14 |
| Journal | Heterocycles |
| Volume | 76 |
| Issue number | 2 |
| DOIs | |
| Publication status | Published - Nov 1 2008 |
Keywords
- 4-Chloro-2-azetidinone
- Carbapenem
- Electrooxidative Chlorination
- Electrooxidative Desulfurization/Chlorination
- Rring Opening
ASJC Scopus subject areas
- Analytical Chemistry
- Pharmacology
- Organic Chemistry
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Kuroboshi, M., Miyada, M., Tateyama, S., & Tanaka, H. (2008). Electrooxidative desulfurization/chlorination. A facile synthesis of 4-chloro-2-azetidinones, a potent intermediate for carbapenems. Heterocycles, 76(2), 1471-1484. https://doi.org/10.3987/COM-08-S(N)110