A new multicomponent reaction MCR4 for the synthesis of analogs of staurosporine

Mati Gelman, Tlalit Massarano, Ronit Lavi, Gerardo Byk

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish
Pages (from-to)505-517
Number of pages13
JournalCurrent Organic Chemistry
Volume22
Issue number5
DOIs
StatePublished - 2018
Externally publishedYes

Keywords

  • Hexa-substituted benzene
  • Isocyanide
  • Meldrum’s acid
  • Multicomponent reaction
  • Staurosporine
  • Tetramic acid
  • Ugi

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