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Stereoselective Synthesis of cis- and trans-3,4-Dihydro-3,4,8-trihydroxynaphthalen-1(2H)-one

✍ Scribed by Emmanuel Couché; Abdellatif Fkyerat; Raffaele Tabacchi

Publisher
John Wiley and Sons
Year
2009
Tongue
German
Weight
416 KB
Volume
92
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

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A short and efficient protocol for the stereoselective synthesis of racemic trans‐ and __cis‐3,4‐dihydro‐3,4,8‐trihydroxynaphthalen‐1(2__H)‐one (1 and 2, resp.), is described, comprising nine and eight steps starting from commercial juglone (=5‐hydroxynaphthalene‐1,4‐dione; 12) (Scheme 4). Furthermore, an attempt to obtain 1 and 2 via phthalide annulation as the key step (Schemes 2 and 3) and a regioselective oxidation of the intermediate 1,2,3,4‐tetrahydronaphthalene‐1,2,4,5‐tetrols 27 and 28 with activated MnO~2~ were carried out (Scheme 4).

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