Efficient Total Syntheses of the Oligopeptide Antibiotics Netropsin and Distamycin

Article abstract of DOI:10.1021/jo00220a019

New and efficient total syntheses of the natural oligopeptide antiviral antibiotics netropsin and distamycin are described.These procedures feature a different strategy of introduction of the terminal groups from that used hitherto, high yield coupling steps, improvements in the Pinner reaction for introducing the amidine moiety, and the novel use of N-formylimidazole for introduction of the formyl moiety in distamycin.The methods also avoid column chromatography with the attendant contamination of the oligopeptide hydrochlorides with inorganic salts eluted from adsorbents.The synthetic procedures are general and may be adapted to the synthesis of related oligopeptide structures.