Chemoenzymatic Synthesis of Triazololactams Structurally Related to Pancratistatin

Abstract

Four tricyclic lactams that structurally resemble alkaloids with the pancratistatin skeleton were synthetized from bromobenzene by a chemoenzymatic strategy. The sequence involved enzymatic dihydroxylation, efficient stereodirected oxidation of double bonds, inter- or intramolecular Huisgen cycloaddition, and a solvent-free cyclization. The complex structures were obtained in high chemical and optical purity and may be good candidates for biological testing.