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

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

Journal Name: Current Organic Chemistry

Volume 22 , Issue 5 , 2018

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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.

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Article Details

VOLUME: 22
ISSUE: 5
Year: 2018
Page: [505 - 517]
Pages: 13
DOI: 10.2174/1385272821666170817110101
Price: $58

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