The synthesis and NMR analysis of a novel highly constrained scaffold is described. The 14-membered macrocyclic ring structure was inspired by many medicinally relevant natural products that also contain the bi-aryl ether moiety. The synthesis required only commercially available starting materials and involved a base mediated SNAr cyclization. A conformational search,,vas performed, which indicated a strong preference for a single conformation, which was consistent with observed ROE signals by NMR. (C) 2004 Elsevier Ltd. All rights reserved.