Synthesis of β-dimorphecolic acid exploiting highly stereoselective reduction of a side-chain carbonyl group in a π-allyltricarbonyliron lactone complex

Abstract

A highly enantioselective synthesis of β-dimorphecolic acid 1 is reported. The synthesis features a diastereoselective reduction of the ketone 4, in which the tricarbonyliron lactone tether induces a 1,5 transfer of chirality, followed by a stereoselective decarboxylation to create all the stereochemical elements of 1. Selective oxidation of the primary alcohol in the diol 17 serves to introduce the acid functionality.