Organocopper Chemistry of Quinone Bisketals. Application to the Synthaais of Isoprenoid Quinone Systems

Article abstract of DOI:10.1021/jo01291a002

The reactions of organocuprates of 1,4-benzoquinone and 1,4-naphthoquinone bisketals are reported.These reagents, formed from the corresponding lithium reagent, cuprous iodide, and dimethyl sulfide react efficiently with allylic bromides (allyl, prenyl, geranyl, and phytyl), often with utilization of greater than one R group of the R₂CuLi.Their reactions with acid chlorides and benzyl bromide proceed with acceptable efficiency, but they are unreactive toward a number of other substrates.The utility of this chemistry in the synthesis of menaquinone-2, phylloquinone,cymopol, and cymopol methyl ether is described.