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 |
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ASJC Scopus subject areas
- Molecular Medicine
- Pharmacology
Cite this
Ester-imine condensations : Preparation of racemic intermediates for the synthesis of the carbapenem antibiotics PS-5 and PS-6. / Ha, Deok-Chan; Hart, D. J.
In: Journal of Antibiotics, Vol. 40, No. 3, 01.01.1987, p. 309-319.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Ester-imine condensations
T2 - Preparation of racemic intermediates for the synthesis of the carbapenem antibiotics PS-5 and PS-6
AU - Ha, Deok-Chan
AU - Hart, D. J.
PY - 1987/1/1
Y1 - 1987/1/1
N2 - 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.
AB - 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.
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UR - http://www.scopus.com/inward/citedby.url?scp=0023113036&partnerID=8YFLogxK
M3 - Article
C2 - 3570984
AN - SCOPUS:0023113036
VL - 40
SP - 309
EP - 319
JO - Journal of Antibiotics
JF - Journal of Antibiotics
SN - 0021-8820
IS - 3
ER -