First total synthesis of oteromycin utilizing one-pot four-step cascade reaction strategy

Abstract

The first total synthesis of oteromycin was investigated. Our previously reported convergent strategy for the synthesis of α-acyl-γ-hydroxy-γ-lactams was first applied for the total synthesis, however, the final deprotection of the methoxyaminal moiety could not be achieved since an unexpected intramolecular Diels–Alder (IMDA) reaction occurred. Therefore, a novel one-pot four-step cascade reaction starting from α-selenolactam was investigated. The efficient synthetic strategy was successfully developed to afford the desired oteromycin, and its complete structure elucidation including the stereochemistry at C24 position was also accomplished.