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  • Title: Stereocontrolled synthesis of anticancer beta-lactams via the Staudinger reaction.
    Author: Banik BK, Banik I, Becker FF.
    Journal: Bioorg Med Chem; 2005 Jun 01; 13(11):3611-22. PubMed ID: 15862989.
    Abstract:
    Stereocontrolled synthesis of novel beta-lactams using polyaromatic imines following the Staudinger reaction has been accomplished. The effects of domestic microwave irradiation on this type of reaction have been investigated. Formation of trans-beta-lactams has been explained through isomerization of the enolates formed during the reaction of acid chloride (equivalent) with imines in the presence of triethylamine. A donor-acceptor complex pathway is believed to be involved in the formation of cis-beta-lactams. The effect of a peri hydrogen has been found to be significant in controlling the stereochemistry of the resulting beta-lactams. SAR has identified beta-lactams with anticancer activity. The presence of an acetoxy group has proven obligatory for their anticancer activity.
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