- Biarylmethane and fused heterocyclic arene synthesis via in situ generated o - And/or p -naphthoquinone methides
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o- and/or p-naphthoquinone methides (NQMs) can be selectively prepared by the ring opening of 1-(siloxymethyl)-1,4-epoxy-1,4-dihydronaphthalene derivatives based on a substituent effect at the 4 position of the substrates. The 4-alkyl- or silyl-substitute
- Sawama, Yoshinari,Kawajiri, Takahiro,Asai, Shota,Yasukawa, Naoki,Shishido, Yuko,Monguchi, Yasunari,Sajiki, Hironao
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p. 5556 - 5565
(2015/06/16)
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- Synthesis, and cyclization to aurones and flavones, of alkoxy-substituted aryl, arylalkynyl ketones
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Acylation of 1,3,5-tribenzyloxybenzene with alkoxy-substituted phenylpropioloyl chlorides provides the corresponding aryl alkoxylarylalkynyl ketones in which one of the benzyl groups has been removed. Cyclization of these phenolic ketones using basic reagents (potassium carbonate in acetone is best) provides the corresponding aurone system. When the phenolic group of the alkynyl ketones is protected as the t-butyldimethylsilyl ether followed by cyclization, using 18-crown-6 and potassium fluoride, mixtures of the corresponding aurones and flavones are produced. A by-product from the formation of the ketones is the corresponding β-chlorochalcone, which can also be cyclized to an aurone product using basic conditions. Similarly, the t-butyldimethylsilyl ethers of the HCl adducts can also be cyclized to a mixture of the corresponding aurones and flavones. CSIRO 2008.
- Kerr, Penelope J.,Pyke, Simon M.,Ward, A. David
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p. 350 - 358
(2008/09/19)
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- Further Total Syntheses of Chlorine-containing Lichen Xanthones
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The unambiguous total synthesis of eight chlorine-containing lichen xanthones by ring closure of appropriately substituted benzophenones is described.
- Fitzpatrick, Leigh,Sala, Tony,Sargent, Melvyn V.
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