Abstract
A fast and efficient synthesis of [2-13C]phloroglucinol in six steps from acyclic, non-aromatic precursors is presented, with regioselective placement of a 13C-atom in the aromatic ring. The 13C-label was introduced by reaction of [13C]methyl iodide with methyl 4-chloroformyl butyrate. Cyclization via an intramolecular Claisen condensation, followed by aromatization gave [2-13C]resorcinol. Following subsequent methylation of the hydroxyl groups, the third hydroxyl group was introduced using an iridium-catalysed C–H activation/borylation/oxidation procedure. Demethylation then yielded the desired [2-13C]phloroglucinol. Copyright © 2010 John Wiley & Sons, Ltd.
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