A convenient synthesis of monpain trimethylether

Synthesis, Antioxidant and Cytotoxic Activities of Novel Naphthoquinone Derivatives from 2,3-Dihydro-2,3-Epoxy-1,4- Naphthoquinone

“…Thus, several methods were reported for the synthesis of hydroxynaphthoquinone compounds [31,32]. In view of the above mentioned findings and in continuation of our work, we report herein the use of 2,3-dihydro-2,3-epoxy-1,4-naphthoquinone (4) [33,34] as a key starting material for the synthesis of various novel heterocycles incorporated 1,4-naphthoquinone moiety.…”

Hydroxyquinones: Synthesis and Reactivity

“…SeO 2 oxidized the proper tetralone derivative to the corresponding orthoquinone and solid KO 2 converted the latter to the desired hydroxynaphthoquinone. This approach found application to the synthesis of 5,7,8-trimethoxy-1,4-naphthoquinone (45), monpain trimethyl ether [33]. (Scheme 20)…”

First Total Synthesis of Malvone A and Formal Syntheses of Boryquinone and Hybocarpone Using a Concise Strategy for Construction of Unsymmetrical Naphthoquinones

“…In our hands, the Thomson, Ameer, and Bekaert procedures proved untenable; none afforded satisfactory yields in our hands. 8,9,12 Inspired by some recent work of Jacobsen, 14 we opted to employ the oxidation of the atetralone 9a with selenium dioxide, providing the o- quinone 10 in a 73% yield (Scheme 2). Further reduction of this material with sodium borohydride and in situ bisacylation with acetyl anhydride produces the bisacyl ester.…”

“…Bekaert improved the yield of the Thomson process by initial selenium dioxide oxidation of a-tetralone followed by a second potassium superoxide oxidation. 9 Anufriev subsequently reported a method employing an admixture of manganese dioxide in concentrated sulfuric acid. 10 For our construction of 1 and 2 we chose to begin with compound 5, which we prepared in 95% yield in one step from commercially available 1,2,4-trimethoxybenzene as previously demonstrated by Carreño 11 (Scheme 1).…”

“…In our hands, the Thomson, Ameer, and Bekaert procedures proved untenable; none afforded satisfactory yields in our hands. 8,9,12 Inspired by some recent work of Jacobsen, 14 we opted to employ the oxidation of the atetralone 9a with selenium dioxide, providing the o-…”