The Journal of Antibiotics
Online ISSN : 1881-1469
Print ISSN : 0021-8820
ISSN-L : 0021-8820
ESTER-IMINE CONDENSATIONS: PREPARATION OF RACEMIC INTERMEDIATES FOR THE SYNTHESIS OF THE CARBAPENEM ANTIBIOTICS PS-5 AND PS-6
DEOK-CHAN HADAVID J. HART
Author information
JOURNAL FREE ACCESS

1987 Volume 40 Issue 3 Pages 309-319

Details
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.
Content from these authors
© Japan Antibiotics Research Association
Previous article Next article
feedback
Top