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이풍래,노영쇠,최오곤 全北大學校 1985 論文集 Vol.27 No.-
4-Methoxy-3-methylphenol, a key compound for the total synthesis of Antitumor antibiotic Nogalamycin was successively prepared. The target molecule was synthesized via six step reaction sequence by transforming three individual functional groups present in the srarting compound, 2,5-dihydroxybenzoic acid. Thus, the carboxyl function of 2,5-dihydroxybenzoic acid was first esterified to give a methyl ester and then the phenolic hydroxyl groups at C-5 and C-2 were transformed into benzyl and methyl ethers, repectively. After reducing the ester function of methyl benzoate, the resulting benzyl alcohol was converted to a tosylate. The tosylate function was then reduced to a methyl group using metal hydride. The remaining benzyloxy group at C-5 was finally deprotected by catalytic hydrogenation to furnish 4-methoxy-3-methylphenol.