An Efficient, Regiospecific Synthesis of 4-Demethoxydaunomycinone and Daunomycinone

YASUMITSU TAMURA; MANABU SASHO; SHUJI AKAI; HISAKAZU KISHIMOTO; JUN-ICHI SEKIHACHI; YASUYUKI KITA

doi:10.1248/cpb.35.1405

YASUMITSU TAMURA, MANABU SASHO, SHUJI AKAI, HISAKAZU KISHIMOTO, JUN-ICHI SEKIHACHI, YASUYUKI KITA

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Keywords: anthracyclinone, 4-demethoxydaunomycinone, daunomycinone, cycloaddition, 4-methoxyhomophthalic anhydride, 4-acetoxyhomophthalic anhydride, ethynylcerium (III) 1

JOURNAL FREE ACCESS

1987 Volume 35 Issue 4 Pages 1405-1412

DOI https://doi.org/10.1248/cpb.35.1405

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Abstract

4-Methoxy and 4-acetoxyhomophthalic anhydrides were prepared by convenient oxidations of homophthalic acid derivatives followed by hydrolysis and dehydrative cyclization. Strong base-induced cycloaddition of these anhydrides to 2-ehloro-6, 6-ethylenedioxy-5, 6, 7, 8-tetrahydro-1, 4-naphthoquinone gave the tetracyclic adducts, which were efficiently converted into 4-demethoxydaunomycinone and daunomycinone.

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