Total Synthesis of Hybocarpone, a Cytotoxic Naphthazarin Derivative from the Lichen Lecanora hybocarpa, and Related Compounds

The concise synthesis of the lichen-derived antitumor agent hybocarpone (1) and its analogs is described. A new synthetic approach is based on the direct oxidative dimerization of the available naphthazarin precursors in the formation of the binaphtho[2,3-b; 2,3-d]furantetraone structure. It was sho...

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Bibliographic Details
Published in:Natural product communications 2014-12, Vol.9 (12), p.1765-1768
Main Authors: Dragan, Sergey V., Pushilin, Michael A., Glazunov, Valery P., Denisenko, Vladimir A., Anufriev, Victor Ph
Format: Article
Language:English
Subjects:
Dimerization
Lichens - chemistry
Magnetic Resonance Spectroscopy
Naphthoquinones - chemical synthesis
Stereoisomerism
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Summary:The concise synthesis of the lichen-derived antitumor agent hybocarpone (1) and its analogs is described. A new synthetic approach is based on the direct oxidative dimerization of the available naphthazarin precursors in the formation of the binaphtho[2,3-b; 2,3-d]furantetraone structure. It was shown that the first step to tetrahydrofuran features is the bridging hindered S*,S* and R*,S* carbon-carbon bonds of the molecules, setting the relative configurations of the 5aS*,6aS*,12aS*,12bS* and 5aS*,6aR*,12aR*,12bS* diastereomers.
ISSN:1934-578X
1555-9475
DOI:10.1177/1934578X1400901227