62008-14-4Relevant academic research and scientific papers
Synthesis of (+/-)-4-Isocymobarbatol by Brominative Cyclization
Tanaka, Akira,Oritani, Takayuki
, p. 516 - 517 (2007/10/02)
The brominative cyclization of 5-bromo-2-geranyl-1,4-benzenediol bismethoxymethyl ether (2) with 2,4,4,6-tetrabromoccylohexydienone was reexamined.This cyclization of 2 resulted in the formation of methoxymethyl ether 10 of 2,4,6-tribromophenol, together with previously described tricyclic compound 7, thus supporting the intervention of oxonium ion 12 in this reaction.An analogous reaction of bismethoxyethoxymethyl ether 4 led to 8.Finally, 7 was converted to (+/-)-4-isocymobarbatol (6).
Organocopper Chemistry of Quinone Bisketals. Application to the Synthaais of Isoprenoid Quinone Systems
Chenard, Bertrand L.,Manning, Michael J.,Raynolds, Peter W.,Swenton, John S.
, p. 378 - 384 (2007/10/02)
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.
