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 satisfa ctory yields by treatment of easily available 3,4-dibromo-2(5H)-furanone ei ther 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 cata lyst 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 compo und with the structure corresponding to that reported for naturally occurri ng rubrolide N. The structure and stereochemistry of these synthetic compou nds have been unambiguously established by NMR techniques. (C) 2001 Elsevie r Science Ltd. All rights reserved.