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

J.H. Buttery, Dieter Wege

Research output: Contribution to journalArticle

15 Citations (Scopus)

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,g-dione (36), a compound possessing the ring system of the naturally occurring quinone ventilone A.
Original languageEnglish
Pages (from-to)409-419
JournalAustralian Journal of Chemistry: an international journal for chemical science
Volume51
Issue numberN/A
DOIs
Publication statusPublished - 1998

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