Recent advances in the stereoselective synthesis of tetrahydrofurans

Abstract

Substituted tetrahydrofurans are commonly occurring substructures found in a broad array of natural products and other biologically active molecules. For example, the annonaceous acetogenins are a large family of natural products bearing tetrahydrofuran cores.1 Tetrahydrofuran moieties are also found in many other classes of natural products including lignans,2 polyether ionophores3 and macrodiolides.4 These substances exhibit a diverse range of biological activities including antitumor, antihelmic, antimalarial, antimicrobial, and antiprotozoal. Due to the importance of these molecules, considerable effort has been devoted towards the development of methods for the stereoselective construction of substituted tetrahydrofurans.5 This review covers the important transformations that have been used in the stereoselective synthesis of tetrahydrofurans, with emphasis placed on literature published between 1993–2005. A broad array of new methods developed over the past twelve years are described, as well as recent advances in older reactions that are widely used. The coverage of this review is limited to the synthesis of tetrahydrofurans; methods that generate furans, dihydrofurans, and benzofurans are not discussed.