Selective synthesis of (Z)-4-aryl-5-[1-(aryl)methylidene]-3-bromo-2(5H)-furanones

4-Aryl-3-bromo-2(5H)-furanones have been selectively synthesized in satisfactory yields by treatment of easily available 3,4-dibromo-2(5H)-furanone either with arylboronic acids in the presence of Ag2O and a catalytic amount of PdCl2(MeCN)(2) or with aryl(trialkyl)stannanes in the presence of a catalyst precursor consisting of AsPh3 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(5H)-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. (C) 2001 Elsevier Science Ltd. All rights reserved.