Author:
Buttery Jarrod H.,Wege Dieter
Abstract
Adducts derived from the aryne
3,6-dimethoxy-4,5-methylenedioxy-1,2-didehydrobenzene (19) with furan and
2-methoxyfuran have been converted into
5,8-dimethoxy-6,7-methylenedioxy-1,2-naphthoquinone (22) and
5,8-dimethoxy-6,7-methylenedioxy-1,4-naphthoquinone (24) respectively. The
trapping of (19) with
1H,3H-furo[3,4-c]furan
(38) yielded an unstable adduct (37), which on acid-catalysed ring opening and
subsequent oxidation was transformed into
5,8-dimethoxy-6,7-methylenedioxynaphtho[2,3-c]furan-4,9-dione
(36), a compound possessing the ring system of the naturally occurring quinone
ventilone A.
Cited by
18 articles.
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1. Advances in the Synthesis of Naphthalene Rings and Their Derivatives by Diels-Alder Reaction;Journal of Organic Chemistry Research;2023
2. Access to 1,2,3,4-Tetraoxygenated Benzenes via a Double Baeyer–Villiger Reaction of Quinizarin Dimethyl Ether: Application to the Synthesis of Bioactive Natural Products from Antrodia camphorata;The Journal of Organic Chemistry;2016-04-01
3. ChemInform Abstract: Some Transformations of Adducts of 3,6-Dimethoxy-4,5-methylenedioxy-1,2-didehydrobenzene and Furans. An Approach to the 5,8-Dimethoxy-6,7-methylenedioxynaphtho[2,3-c]furan-4,9-dione Ring System of Ventilone A.;ChemInform;2010-06-19
4. Synthesis of 2,5-Dihydrofuran-Fused Quinones from Ether-Tethered Diiododiyne;The Journal of Organic Chemistry;2009-04-29
5. An approach to the synthesis of furanoheliangolides through Diels–Alder reactions;Tetrahedron Letters;2008-02