Total Synthesis of a Monomeric Phloroglucinol Derivative Isolated from <i>Myrtus communis</i>

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Author(s)

Abstract

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.

Journal

  • Chemistry Letters

    Chemistry Letters 44(4), 445-447, 2015

    The Chemical Society of Japan

Codes

  • NII Article ID (NAID)
    130005062135
  • Text Lang
    ENG
  • ISSN
    0366-7022
  • Data Source
    J-STAGE 
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