Reactions of 3-(Phenylthio)-3-buten-2-one with Cycloalkanones. A New Approach to Fused Phenols

Article abstract of DOI:10.1021/jo00346a012

Synthesis and properties of 3-(phenylthio)-3-buten-2-one (7) have been described.The butenone 7 reacted with lithium cycloalkanone enolates to give ketols 14 or diketones 15 in good yields, which were easily transformed into fused phenols 17 by the treatment with p-toluenesulfonic acid or sodium ethoxide, respectively.Oxidative elimination of the sulfenyl group of 14a afforded also 2-naphthol 17a.Tetrahydronaphthalene 23, a key intermediate of calamenene 1a and calamenenal 1b, was successfully synthesized by this approach by starting from l-carvone (19).Bicyclo<2.2.2>octanone 25 was obtained in the reaction of 7 with kinetic enolate of 2-cyclohexen-1-one in 84percent yield.