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The first synthesis of [2‐ 13 C]phloroglucinol
Author(s) -
Marshall Laura J.,
Cable Karl M.,
Botting Nigel P.
Publication year - 2010
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.1788
Subject(s) - chemistry , phloroglucinol , demethylation , regioselectivity , methyl iodide , resorcinol , medicinal chemistry , electrophilic aromatic substitution , intramolecular force , iodide , borylation , hydroxylation , aromatization , ring (chemistry) , stereochemistry , organic chemistry , catalysis , biochemistry , gene expression , alkyl , aryl , dna methylation , gene , enzyme
A fast and efficient synthesis of [2‐ 13 C]phloroglucinol in six steps from acyclic, non‐aromatic precursors is presented, with regioselective placement of a 13 C‐atom in the aromatic ring. The 13 C‐label was introduced by reaction of [ 13 C]methyl iodide with methyl 4‐chloroformyl butyrate. Cyclization via an intramolecular Claisen condensation, followed by aromatization gave [2‐ 13 C]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‐ 13 C]phloroglucinol. Copyright © 2010 John Wiley & Sons, Ltd.
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