Copper-Catalyzed Radical Cyclization To Access 3-Hydroxypyrroloindoline: Biomimetic Synthesis of Protubonine A
Organic Letters2014Vol. 16(12), pp. 3276–3279
Citations Over TimeTop 10% of 2014 papers
Abstract
An unprecedented copper-catalyzed intramolecular radical cyclization was developed for the synthesis of 3-hydroxypyrroloindoline skeletons in excellent yields. The 3-hydroxyl group was introduced by trapping the radical intermediate with molecular oxygen or TEMPO. This process represents a unique radical oxidation pathway for tryptamine/tryptophan derivatives and allows a rapid biomimetic synthesis of natural product protubonine A.
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