The First Synthesis of an Epidiselenodiketopiperazine
ABSTRACT Epidithiodiketopiperazines (ETPs) are natural products (e.g., gliotoxin) with varied and important biological activity, which often is attributed to the redox properties of the disulfide moiety. As such, analogs with altered redox properties and similar structural characteristics would be of value to biological investigations. The use of an ETP as the point of departure in the first synthesis of an epidiselenodiketopiperazine (ESeP) and its activity against Mycobacterium tuberculosis (MTB) is reported.
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ABSTRACT: A novel and efficient synthesis of benzo[f]isoindole-4,9-diones through the I2-promoted cyclization reaction of N-substituted amino acid esters and quinones has been realized successfully via an unprecedented 1,3-dipolar cycloaddition using KF as the base. Different substituted amino esters were found able to react with quinones through a cycloaddition reaction to afford 2-substituted benzo[f]isoindole-4,9-diones. The unexpected, short, attractive and direct synthesis of these interesting compounds is important and relevant, and provides an extremely preferable method for the synthesis of 2-substituted benzo[f]isoindole-4,9-diones.RSC Advances 01/2013; 3(48):25840. DOI:10.1039/c3ra44095h · 3.71 Impact Factor