Progress in Lewis-Acid-Templated Diels–Alder Reactions

Abstract

The synthesis of natural products with complicated architectures often requires the use of segments with functional groups that can be structurally transformed with the desired stereogenic centers. Bicyclic γ-lactones have great potential as a suitable segment for natural product synthesis. However, the stereoselective construction of such functionalized bicyclic γ-lactones is not as straightforward as one might expect. The template-mediated Diels–Alder reaction is one of the most powerful and versatile methods for providing bicyclic γ-lactones with high regioselectivity and stereoselectivity. In this reaction, the diene is linked to the dienophile by a temporary tether, allowing the reaction to proceed efficiently, yielding a product that can be used for natural product synthesis. This review describes some important instances of the template-mediated Diels–Alder reaction and its application to the synthesis of biologically active compounds.