Studies on 2-Aziridinecarboxylic Acid. IV. Total Synthesis of Actinomycin D (C1) <i>via</i> Ring-opening Reaction of Aziridine

Abstract

Abstract Actinomycin D (C1) has been synthesized by a route involving the ester formation between two peptide fragments, (2S,3S)-1-(2-nitro-3-benzyloxy-4-methylbenzoyl)-3-methyl-2-aziridinecarbonyl-d-valylproline t-butyl ester and N-benzyloxycarbonylsarcosyl-N-methylvaline, via a ring-opening reaction of aziridine. Cyclization, followed by reduction and oxidation, gave actinomycin D (C1). The synthetic actinomycin D (C1) was indistinguishable from natural substance as regards physical properties and biological activity.