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Stereoselective Synthesis of <i>cis</i>- and <i>trans</i>-3,4-Dihydro-3,4,8-trihydroxynaphthalen-1(2<i>H</i>)-one
Auteur(s)
Couché, Emmanuel
Fkyerat, Abdellatif
Tabacchi, Raphael
Date de parution
2009
In
Helvetica Chimica Acta, Wiley, 2009/92/5/903-917
Résumé
A short and efficient protocol for the stereoselective synthesis of racemic <i>trans</i>- and <i>cis</i>-3,4-dihydro-3,4,8-trihydroxynaphthalen-1(2<i>H</i>)-one (<b>1</b> and <b>2</b>, resp.), is described, comprising nine and eight steps starting from commercial juglone (=5-hydroxynaphthalene-1,4-dione; <b>12</b>) (<i>Scheme 4</i>). Furthermore, an attempt to obtain <b>1</b> and <b>2</b> via phthalide annulation as the key step (<i>Schemes 2</i> and <i>3</i>) and a regioselective oxidation of the intermediate 1,2,3,4-tetrahydronaphthalene-1,2,4,5-tetrols <b>27</b> and <b>28</b> with activated MnO<sub>2</sub> were carried out (<i>Scheme 4</i>).
Identifiants
Type de publication
journal article
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