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.
Keywords: Staurosporine, multicomponent reaction, Ugi, isocyanide, tetramic acid, hexa-substituted benzene, Meldrum's acid.
Current Organic Chemistry
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.
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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
DOI https://dx.doi.org/10.2174/1385272821666170817110101 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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