Studies on 2-Aziridinecarboxylic Acid. VIII. Total Synthesis of Actinomycin D and Its Serine Analogue via Ring-opening Reaction of 1-Benzyloxycarbonyl-2-aziridinecarboxylic Acid Moiety

Direct synthesis of peptides containing 1-benzyloxycarbonyl-2-aziridinecarboxylic acid were carried out by the reaction of β-hydroxy-α-amino acid peptides with DEAD–TPP reagents, and key O-peptide intermediates of actinomycin D synthesis were prepared via a ring-opening reaction of the aziridine with N-protected dipeptide. Peptide lactone was prepared by the DCC–HOBt method, and the subsequent debenzyl procedure and oxydation procedure gave the title compounds in good yields.