Total Synthesis of a Monomeric Phloroglucinol Derivative Isolated from <i>Myrtus communis</i>
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The first total synthesis of a monomeric phloroglucinol [(1<i>R*</i>,2<i>S*</i>)-2-hydroxy-2-isobutyl-4,4,6,6-tetramethyl-3,5-dioxocyclohexyl acetate] was achieved by stereoselective reduction of a symmetrical α-ketol as a key step. The corresponding <i>cis</i>-stereoisomer of the natural product was synthesized from phloroglucinol via <i>cis</i>-dihydroxylation using OsO<sub>4</sub>. Comparison of <sup>1</sup>H NMR data for synthetic <b>1</b> and <b>2</b> confirmed the <i>trans</i>-stereochemistry of the natural product.
- Chemistry Letters
Chemistry Letters 44(4), 445-447, 2015
The Chemical Society of Japan