Total synthesis of diazaquinomycin A

Article abstract of DOI:10.1016/S0040-4039(97)10589-5

Two concise total syntheses of the diazaanthraquinone antibiotic diazaquinomycin A are reported. The first route features a double hetero Diels-Alder reaction between 2,6-dibromobenzoquinone and 2-methyl-2-hexenal dimethylhydrazone, aromatization by a novel, one-pot N-oxidation/elimination procedure with percarbamide in trifluoroacetic acid, and double N-oxidation followed by rearrangement to a double lactam system. The key step of the second route is a hetero Diels-Alder reaction between 2-methyl-2-hexenal dimethylhydrazone and 3-methyl-4-propyl-1H-quinoline-2,5,8-trione.