Generic placeholder image

Current Organic Chemistry


ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

Research Article

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

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

Volume 22, Issue 5, 2018

Page: [505 - 517] Pages: 13

DOI: 10.2174/1385272821666170817110101

Price: $65


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.

« Previous
Graphical Abstract

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy