Synthesis of the Benz[a]anthraquinone Core of Angucyclinone Antibiotics

Synthesis of the Benz[a]anthraquinone Core of Angucyclinone Antibiotics

A general method for the synthesis of benz[a]anthraquinones is reported. The key step is a catalytic cobalt-mediated [2+2+2]-cycloaddition of a triyne, which affords an angularly substituted tetracycle. Oxidation of this core gives the typical structure of angucyclinone antibiotics.

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Veröffentlicht in:Organic letters 2003-03, Vol.5 (6), p.843-844
Hauptverfasser: Kalogerakis, Aris, Groth, Ulrich
Format: Artikel
Sprache:eng
Schlagworte:
Anthraquinones - chemical synthesis
Anti-Bacterial Agents - chemical synthesis
Benz(a)Anthracenes - chemical synthesis
Catalysis
Cobalt
Cyclization
Indicators and Reagents
Oxidation-Reduction
Streptomyces - chemistry
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Zusammenfassung:A general method for the synthesis of benz[a]anthraquinones is reported. The key step is a catalytic cobalt-mediated [2+2+2]-cycloaddition of a triyne, which affords an angularly substituted tetracycle. Oxidation of this core gives the typical structure of angucyclinone antibiotics.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0274920