Next Article in Journal
Synthesis and Characterization of the Complexes of Pentane-2,4-dione with Nickel(II) and Cobalt(III): [Ni(acac)2]·0.5CH3OH and [Co(acac)2NO3]·2H2O (acac = Pentane-2,4-dione)
Previous Article in Journal
Quantum Chemical and Experimental Studies on the Mechanism of Alkylation of β-Dicarbonyl Compounds. The Synthesis of Five and Six Membered Heterocyclic Spiro Derivatives
Molecules 2004, 9(11), 939-948; doi:10.3390/91100939

Asymmetric Synthesis and Antimicrobial Activity of Some New Mono and Bicyclic β-Lactams

1,* , 1 and 2
1 Chemistry Department, College of Sciences, Shiraz University, Shiraz 71454, Iran 2 Institute of Standards and Industrial Research of Iran, Shiraz 71447, Iran
* Author to whom correspondence should be addressed.
Received: 24 September 2004 / Accepted: 31 August 2004 / Published: 30 November 2004
View Full-Text   |   Download PDF [214 KB, uploaded 18 June 2014]   |   Browse Figures


Reaction of the amino acid D-phenylalanine ethyl ester (4) with cinnamaldehyde gave chiral Schiff base 5, which underwent an asymmetric Staudinger [2+2] cycloaddition reaction with phthalimidoacetyl chloride to give the monocyclic β-lactam 6 as a single stereoisomer. Ozonolysis of 6 followed by reduction with lithium aluminum tri(tert-butoxy) hydride afforded the hydroxymethyl β-lactam 8. Treatment of 8 with methansulfonyl chloride gave the mesylated monocyclic β-lactam 9, which was converted to the bicyclic β-lactam 10 upon treatment with 1,8-diazabicyclo[5,4.0] undec- 7-ene (DBU). Deprotection of the phthalimido group in β-lactams 6 and 10 by methylhydrazine and subsequent acylation of the free amino β-lactams with different acyl chlorides in the presence of pyridine afforded mono and bicyclic β-lactams 14a-d and 15a-d respectively. The compounds prepared were tested against Escherichia coli, Staphilococcus citrus, Klebsiella pneumanie and Bacillus subtillis. Some of these compounds showed potential antimicrobial activities.
Keywords: D-Phenylalanine; asymmetric induction; chiral Schiff base; DBU; antimicrobial D-Phenylalanine; asymmetric induction; chiral Schiff base; DBU; antimicrobial
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote |
MDPI and ACS Style

Jarrahpour, A.A.; Shekarriz, M.; Taslimi, A. Asymmetric Synthesis and Antimicrobial Activity of Some New Mono and Bicyclic β-Lactams. Molecules 2004, 9, 939-948.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here


[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert