PubMed · 13494161
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E HANNIG, G LEUSCHNER. 1957. [Some alpha-alkylated basic propiophenones].. https://pubmed.ncbi.nlm.nih.gov/13494161/
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(--)-Muricatacin, a potent cytotoxic (4R,5R)-5-hydroxyheptadecan-4-olide, has been synthesized through alpha-C--H hydroxyalkylation and alpha'-C--H oxidation of tetrahydrofuran. This study presents a novel method for C--H bond functionalization as a means for preparing gamma-(hydroxyalkyl)-gamma-butyrolactones.
[reaction: see text] Representative B-butyl- and B-methyl-1,3,2-oxazaborolidines derived from ephedrine and norephedrine were prepared in good yield and excellent purity by one-pot treatment of B-H oxazaborolidines with the corresponding organolithium reagent and subsequent hydrolysis of the cyclic borohydride intermediate with anhydrous ammonium chloride.
[reaction: see text] A mild and general palladium-catalyzed insertion of 1,2-diethoxy-1,1,2,2-tetramethyldisilane into a variety of aryl bromides affords the aryldimethylsilyl ethers in high yields. Hydrolysis of the ethers under pH-optimized conditions results in the exclusive formation of the desired aryldimethylsilanols.