Abstract
The lithium enolates of ethyl butyrate (7) and ethyl isovalerate (19) react with N-p-methoxyphenylcinnamaldimine (8) in tetrahydrofuran (THF) - hexamethylphosphoric triamide (HMPA) to afford predominantly trans β-lactams 9 (67%) and 20 (78%), respectively. β-Lactam 9 was converted to PS-5 (5) intermediate 18 in 21% overall yield (8 steps). β-Lactam 20 was converted to PS-6 (6) analog 28 in 22% overall yield using an eight step sequence.
| Original language | English |
|---|---|
| Pages (from-to) | 309-319 |
| Number of pages | 11 |
| Journal | Journal of Antibiotics |
| Volume | 40 |
| Issue number | 3 |
| Publication status | Published - 1987 Jan 1 |
| Externally published | Yes |
ASJC Scopus subject areas
- Molecular Medicine
- Pharmacology
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Ha, D-C., & Hart, D. J. (1987). Ester-imine condensations: Preparation of racemic intermediates for the synthesis of the carbapenem antibiotics PS-5 and PS-6. Journal of Antibiotics, 40(3), 309-319.