Portal de Periódicos da CAPES

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

1992; Issue: 11 Linguagem: Inglês

10.1039/p19920001365

2050-8255

Derek H. R. Barton, Dervilla M. X. Donnelly, Jean‐Pierre Finet, Patrick J. Guiry,

Synthesis of heterocyclic compounds

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.