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