A New Multicomponent Reaction MCR4 for the Synthesis of Analogs of Staurosporine

Title:A New Multicomponent Reaction MCR4 for the Synthesis of Analogs of Staurosporine

Volume: 22 Issue: 5

Author(s): Mati Gelman, Tlalit Massarano, Ronit Lavi and Gerardo Byk*

Affiliation:

• Department of Chemistry, Exact Sciences Faculty, Bar Ilan University, Ramat Gan,Israel

Keywords: Staurosporine, multicomponent reaction, Ugi, isocyanide, tetramic acid, hexa-substituted benzene, Meldrum's acid.

Abstract: Background: We report a novel MCR4 useful for generating chiral analogs of staurosporine a promiscuous and potent protein kinases inhibitor.

Method: Our strategy introduces the use of substituted tetramic acids as chiral precursors which together with an aldehyde, an isocyanide, a dienophile and a Lewis acid lead to hexa-substituted benzenes in one pot.

Conclusion: Interestingly, the use of chiral precursors not only allowed obtaining a stereo- controlled reaction, but also observing unusual atropo-diastereomers with axial chirality. The reaction can be carried out both under thermal or microwave conditions. The methodology is demonstrated for a panel of aldehydes, tetramic acids, isocyanides and dienophiles.

Cite this article as:

Gelman Mati , Massarano Tlalit , Lavi Ronit and Byk Gerardo *, A New Multicomponent Reaction MCR4 for the Synthesis of Analogs of Staurosporine, Current Organic Chemistry 2018; 22(5) . https://dx.doi.org/10.2174/1385272821666170817110101