Phthalides reactions with arynes

Another route to anthraquinones has been devised which relies on the addition of carbanions (22) derived from phthalides to arynes (81JCS(P1)2120). For the formation of anthraquinone (23) itself, phthalide was treated with 2.2 equivalents of lithium diisopropyl-amide in THF. Bromobenzene was then added and the reaction mixture warmed to room... 

Unsymmetrically substituted anthraquinones have been synthesised through addition of the isobenzofuranone 52 to arynes generated in situ from haloarenes, the regioselectivity of the reaction being controlled by substituents in the aryne moiety [61]. This approach is unlikely to allow regiospecific synthesis of anthracyclinones other than 11-deoxy analogues, but the unsubstituted phthalide 51 has been condensed with 68 to give 69, a precursor of 4-demethoxydaunomycinone 6. 

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See also in sourсe #XX -- [ ]

See also in sourсe #XX -- [ , ]

See also in sourсe #XX -- [ , ]

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