Utilization of a copper-catalyzed diaryl ether synthesis for the preparation of verbenachalcone

2-Hydroxy-2'-methoxydiphenyl ethers were efficiently assembled utilizing a catalytic copper mediated coupling of 2-benzyl-oxybromobenzene derivatives and 2-methoxyphenol derivatives in the presence of cesium carbonate in pyridine followed by debenzylation. Utilization of this method allowed for a concise synthesis of verbenachalcone, a compound reported to enhance nerve growth factor's ability to stimulate neurite outgrowths in PC12D cells. Initial SAR data is also presented. (C) 2002 Elsevier Science Ltd. All rights reserved.