F. Bellina, C. Anselmi, S. Viel
Dec 10, 2001
Citations
0
Influential Citations
48
Citations
Journal
Tetrahedron
Abstract
Abstract 4-Aryl-3-bromo-2(5 H )-furanones have been selectively synthesized in satisfactory yields by treatment of easily available 3,4-dibromo-2(5 H )-furanone either with arylboronic acids in the presence of Ag 2 O and a catalytic amount of PdCl 2 (MeCN) 2 or with aryl(trialkyl)stannanes in the presence of a catalyst precursor consisting of AsPh 3 and a Pd(II) or a Pd(0) compound. These monobromo derivatives have been then used as precursors to a variety of ( Z )-4-aryl-5-[1-(aryl)methylidene]-3-bromo-2(5 H )-furanones including the compound with the structure corresponding to that reported for naturally occurring rubrolide N. The structure and stereochemistry of these synthetic compounds have been unambiguously established by NMR techniques.