Irreversible endo-selective diels-alder reactions of substituted alkoxyfurans: a general synthesis of endo-cantharimides

Chemistry : a European Journal
Robert W FosterTom D Sheppard

Abstract

The [4+2] cycloaddition of 3-alkoxyfurans with N-substituted maleimides provides the first general route for preparing endo-cantharimides. Unlike the corresponding reaction with 3H furans, the reaction can tolerate a broad range of 2-substitued furans including alkyl, aromatic, and heteroaromatic groups. The cycloaddition products were converted into a range of cantharimide products with promising lead-like properties for medicinal chemistry programs. Furthermore, the electron-rich furans are shown to react with a variety of alternative dienophiles to generate 7-oxabicyclo[2.2.1]heptane derivatives under mild conditions. DFT calculations have been performed to rationalize the activation effect of the 3-alkoxy group on a furan Diels-Alder reaction.

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Citations

Jun 11, 2015·Angewandte Chemie·Richard J BurfordShih-Yuan Liu
Aug 28, 2018·European Journal of Organic Chemistry·Samantha M GibsonTom D Sheppard
Mar 31, 2017·Organic & Biomolecular Chemistry·Mikail E AbbasovDaniel Romo
May 25, 2021·International Journal of Pharmaceutics·Adeolu Oluwasanmi, Clare Hoskins
Aug 13, 2021·Green Chemistry : an International Journal and Green Chemistry Resource : GC·Răzvan C CiocPieter C A Bruijnincx
Jun 23, 2018·Bioconjugate Chemistry·Andre H St AmantJavier Read de Alaniz

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Methods Mentioned

BETA
column chromatography
X-ray

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