- Depsidone Synthesis. Part 21. A New Synthesis of Grisa-2',5'-diene-3,4'-diones
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Treatment of suitably substituted methyl 2-phenoxybenzoates with titanium(IV) chloride and dry hydrogen chloride afforded grisa-2',5'-diene-3,4'-diones in high yield.The structures of these compounds followed from their thermal stability, their methanolysis to methyl 2-(4-hydroxyphenoxy)benzoates, and their reductive cleavage to 2,4'-dihydrobenzophenones.Treatment of the benzophenones with base gave xanthones.An attempt to synthesize dehydrogriseofulvin (1) by this method failed.
- Sargent, Melvyn V.
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p. 403 - 411
(2007/10/02)
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- Synthesis of Grisa-2',5'-dien-3,4'-diones by Intramolecular ipso-Substitution
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Appropriately substituted o-phenoxybenzoic esters on treatment with dry hydrogen chloride and titanium(IV) chloride in dichloromethane yield grisa-2',5'-dien-3,4'-diones by intramolecular ipso-substitution.
- Sargent, Melvyn
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