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An efficient, regiospecific synthesis of 4-demethoxydaunomycinone and daunomycinone
Chemical and pharmaceutical bulletin
4-Methoxy and 4-acetoxyhomophthalic anhydrides were prepared by convenient oxidations of homophthalic acid derivatives followed by hydrolysis and dehydrative cyclization. Strong baseinduced cycloaddition of these anhydrides to 2-ehloro-6,6-ethylenedioxy-5,6,7,8-tetrahydro-1,4naphthoquinone gave the tetracyclic adducts, which were efficiently converted into 4-demethoxydaunomycinone and daunomycinone.doi:10.1248/cpb.35.1405 fatcat:adysnelvjzcxbdcrt3icsbjkuy