Issue 11, 1992

Application of aryllead(IV) derivatives to the preparation of 3-aryl-4-hydroxy-1-benzopyran-2-ones

Abstract

Aryllead triacetates are chemoselective and regioseiective reagents for the preparation of 3-aryl-4-hydroxy-1-benzopyran-2-ones in good to excellent yields by C-3 arylation of the preformed 4-hydroxy-1-benzopyran-2-one ring. This approach was applied to the high-yielding synthesis of naturally occurring examples. A radical mechanism was discounted and the mechanism proposed involves the ligand coupling of an intermediate possessing an enolate-to-lead bond to afford arylated products.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1992, 1365-1375

Application of aryllead(IV) derivatives to the preparation of 3-aryl-4-hydroxy-1-benzopyran-2-ones

D. H. R. Barton, D. M. X. Donnelly, J. Finet and P. J. Guiry, J. Chem. Soc., Perkin Trans. 1, 1992, 1365 DOI: 10.1039/P19920001365

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