Synthesis of polyhydroxylated ester analogs of the stilbene resveratrol using decarbonylative Heck couplings

doi:10.1016/j.tetlet.2006.05.065

Tetrahedron Letters

Volume 47, Issue 32, 7 August 2006, Pages 5811-5814

https://doi.org/10.1016/j.tetlet.2006.05.065 Get rights and content

Abstract

Protected 3,5-hydroxy-benzoyl chlorides 3 were coupled with styrenes 4 to give hydroxylated stilbenes, analogs of resveratrol, an important antioxidant disease preventative agent isolated from grape skins and other dietary sources. Levulinate and chloroacetate protecting groups allowed for the selective production of mono- and di-acetate variations under palladium-N-heterocyclic carbene (NHC) catalyzed decarbonylative coupling conditions. Fluorinated analogs were also produced using Heck conditions with bromofluorobenzenes. Human HL-60 cell assays showed the 4′-acetoxy variant 11 to have improved activity (ED₅₀ 17 μM) relative to resveratrol (24 μM).

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Acknowledgements

We are grateful to the BYU Cancer Research Center, for funding.

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Synthesis of polyhydroxylated ester analogs of the stilbene resveratrol using decarbonylative Heck couplings

Abstract

Graphical abstract

Section snippets

Acknowledgements

Tetrahedron Lett.

Lancet

J. Organomet. Chem.

J. Organomet. Chem.

J. Organomet. Chem.

J. Organomet. Chem.

Angew. Chem., Int. Ed.

Tetrahedron Lett.

Synthesis

Org. Lett.

Org. Lett.

Org. Lett.

Tetrahedron

Tetrahedron Lett.

J. Am. Chem. Soc.

J. Org. Chem.

Carcinogenesis

Nature

Nature

Nature Genetics

J. Biol. Chem.