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New Syntheses Of Diaryl Ethers, Tyrosinols, B-Hydroxytyrosinols, L,L-Isodityrosinol And L,L-Isodityrosine-Derived Agents Via The Diels-Alder Reaction, Xianqi Feng

All Graduate Theses and Dissertations, Spring 1920 to Summer 2023

Syntheses of diaryl ethers were approached by use of a Diels-Alder reaction employing a new type of diene attached with an aryloxy group. Thus, 2-methyl-3-phenoxybutadiene (90b ), 2- methoxy-3-phenoxybutadiene (92b) and (4S)-3-(t- butyloxycarbony1)-2 ,2-dimethyl-4-( 4-(3-methoxy-1,3 -butadienyl-2- oxy )phenylmethyl]oxazolidine (93b) were synthesized in ~65% yields by methylenation of the carbonyl function in the corresponding 2- substituted acrylate aryl ester using Tebbe's reagent. The 1,3- bis[(trimethylsilyl)oxy ]-2-phenoxybutadiene (105) was made from 1-phenoxy-2-propanone (101) by a sequence of formylation and enolsilylation. Methyl propiolate (107) and dimethyl acetylenedicarboxylate (113) were heated at reflux with diene 9 0 b and 92b in toluene to provide …