Synthesis of the benz[a]anthraquinone core of angucyclinone antibiotics.
[reaction: see text] 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.
Kalogerakis
Aris
A
Fachbereich Chemie, Universität Konstanz, Fach M-720, Universitaetsstrasse 10, 78457 Konstanz, Germany.
Groth
Ulrich
U
D000880:Anthraquinones / Q000138:chemical synthesis*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D001551:Benz(a)Anthracenes / Q000138:chemical synthesis*; D002384:Catalysis; D003035:Cobalt; D003500:Cyclization; D007202:Indicators and Reagents; D010084:Oxidation-Reduction; D013302:Streptomyces / Q000737:chemistry
D000880:Anthraquinones; D000900:Anti-Bacterial Agents; D001551:Benz(a)Anthracenes; D007202:Indicators and Reagents; D003035:Cobalt; C077646:7,12-benz(a)anthraquinone