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Total Synthesis of Diptoindonesin G via a Highly Efficient Domino Cyclodehydration/Intramolecular Friedel−Crafts Acylation/Regioselective Demethylation Sequence

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journal contribution
posted on 2010-11-19, 00:00 authored by Kyungsun Kim, Ikyon Kim
A highly efficient total synthesis of diptoindonesin G is described employing a domino dehydrative cyclization/intramolecular Friedel−Crafts acylation/regioselective demethylation reaction of aryloxyketone 7 by the action of BCl3 wherein the tetracyclic 6H-anthra[1,9-bc]furan-6-one skeleton was constructed via the 3-arylbenzofuran in a one-pot manner. This is the first example of the strategic combination of these three reactions in a cascade fashion. The routes presented here allow for direct access to diptoindonesin G and its analogues.