Total Synthesis of (±)-Taiwaniaquinol B via a Domino Intramolecular Friedel−Crafts Acylation/Carbonyl α-tert-Alkylation Reaction
Journal of the American Chemical Society2005Vol. 127(38), pp. 13144–13145
Citations Over TimeTop 10% of 2005 papers
Abstract
The first synthesis of taiwaniaquinol B, a 6-nor-5(6-->7)abeoabietane-type diterpenoid exhibiting the uncommon fused 6-5-6 tricyclic carbon skeleton, was accomplished in 15 steps. A Lewis acid-promoted tandem intramolecular Friedel-Crafts/carbonyl alpha-tert-alkylation reaction was exploited as the core strategy for the synthesis of the sterically congested 1-indanone-containing tricyclic structure. This multiple carbon-carbon bond forming reaction exploits the unique reactivity of Meldrum's acid. The facile precursor synthesis makes this a useful methodology for the expedient modification and assembly of sterically congested 1-indanone-containing ring systems.
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