Ester-imine condensations: Preparation of racemic intermediates for the synthesis of the carbapenem antibiotics PS-5 and PS-6

Deok-Chan Ha; D. J. Hart

Ester-imine condensations

Preparation of racemic intermediates for the synthesis of the carbapenem antibiotics PS-5 and PS-6

Deok-Chan Ha, D. J. Hart

Research output: Contribution to journal › Article

14 Citations (Scopus)

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

Fingerprint

Lactams

Carbapenems

Imines

Esters

Hempa

Lithium

PS 5

PS-6

ASJC Scopus subject areas

Molecular Medicine
Pharmacology

Cite this

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.

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

Ha, D-C & Hart, DJ 1987, 'Ester-imine condensations: Preparation of racemic intermediates for the synthesis of the carbapenem antibiotics PS-5 and PS-6', Journal of Antibiotics, vol. 40, no. 3, pp. 309-319.

Ha D-C, Hart DJ. Ester-imine condensations: Preparation of racemic intermediates for the synthesis of the carbapenem antibiotics PS-5 and PS-6. Journal of Antibiotics. 1987 Jan 1;40(3):309-319.

Ha, Deok-Chan ; Hart, D. J. / Ester-imine condensations : Preparation of racemic intermediates for the synthesis of the carbapenem antibiotics PS-5 and PS-6. In: Journal of Antibiotics. 1987 ; Vol. 40, No. 3. pp. 309-319.

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