REGIOSPECIFIC SYNTHESIS OF 1,6- DIMETHY L-9,lO-ANTHRACENEDIONE
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Abstract:
Treatment of acetyl- 1,4-benzoquinone with isoprene gave the corresponding regioselective adduct (I). Rearrangement of the adduct (1) in pyridine and methanol gave 2-acetyl-5, 8-dihydro-6-methyl- 1,4-dihydroxynaphthalene (2). Silver oxide oxidation of the rearranged product (2) gave 2-acetyl-5,8-dihydro- 6-methyl- 1,4naphthalenedione (3). Regioselective addition of trans-piperylene to this compound (3) gave the c&esponding adduct (4). Treatment of the resulting cycloadduct (4) with manganese dioxide gave the regiospecific 1,6- dimethyl-9, 10-anthracenedione (5). Each of the foregoing reactions proceeds in high yield
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Journal title
volume 8 issue 3
pages -
publication date 1997-09-01
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