Journal
ORGANIC LETTERS
Volume 3, Issue 24, Pages 3875-3878Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol0167199
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- NCI NIH HHS [CA-87503] Funding Source: Medline
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[GRAPHICS] Thermolysis of enolizable vinyl quinones in polar, aprotic media provides 2H-chromenes. Experimental evidence supports a two-step mechanism in which enolization is followed by a thermal 6 pi -electrocyclic reaction of an intermediate quinone methide. Application of this method led to the total synthesis of the reputed structure of an Ageratum juvenile hormone. When enolizable vinyl quinones are the products of Stille coupling, the chromene annulation product is obtained directly.
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