Concise Total Synthesis of (−)-Erinapyrone B from D-(+)-Malic Acid

Abstract

<div><p></p><p>A convenient and facile enantioselective synthesis of (−)-erinapyrone B from commercially available D-(+)-malic acid has been achieved in seven steps. One of the key steps in this synthesis was the one-pot reaction of palladium(II)-mediated Wacker-type oxidative cyclization in the presence of a catalytic amount of <i>p</i>-toluenesulphonic acid (<i>p</i>-TsOH) which has been found to be effective for the preparation of enantiopure 2,3-dihydro-4<i>H</i>-pyran-4-one from the corresponding enantiopure β-hydroxyenone via enantio-enriched diketohydroxy intermediate.</p> <p>[Supplementary materials are available for this article. Go to the publisher's online edition of <i>Synthetic Communications®</i> for the following free supplemental resource(s): Full experimental and spectral details.]</p> </div

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