Exploring the reactivity of chiral glycidic amides for their applications in synthesis of bioactive compounds.

Abstract

A new class of chiral sulfonium salts, derived from L- and D-methionine, has been designed and successfully employed in our laboratories for the diastereoselective synthesis of glycidic amides. The epoxy amides obtained were converted cleanly into 1,2-difunctionalized products through oxirane ring-opening reactions with different types of nucleophiles. The resulting ring-opened products represent valuable and useful building blocks for the synthesis of different bioactive products. Thus, the expedient synthesis of clavaminol H as well as the synthesis of key precursors for other bioactive compounds, for example, polyketide-derived natural products, have been achieved, demonstrating the synthetic efficiency and utility of this chemistry.