Total synthesis of diazaquinomycin A

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, aromatiztion by a novel, one-pot N-oxidation/elimination procedure...

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Bibliographic Details
Published in:Tetrahedron letters 1998-02, Vol.39 (7), p.673-676
Main Authors: Pérez, JoséMaría, López-Alvarado, Pilar, Avendaño, Carmen, Menéndez, J.Carlos
Format: Article
Language:English
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Summary: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, aromatiztion 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-1 H-quinoline-2,5,8-trione. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(97)10589-5