Heteroanthracyclines. 1. 4-Demethoxyxanthodaunomycinone (6,7,9,11-tetrahydroxy-9-acetyl-7,8,9,10-tetrahydrobenzo(B)xanthen-12-one)

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Abstract
Two heteroanthracyclinones, namely 4-demethoxyxanthodaunomycinone (29) and its epimer 4-demethoxy-7-epixantho-daunomycinone (30), were synthesized using 2-acetyl-5,8-dimethoxytetralin (12) as starting material. Condensation of 12 with 2-methoxybenzoic acid followed by hydrolysis and oxidative cyclization gave xanthones 17 and 18 which were converted to 19 and 20 for the purpose of separation and structure assignment by dipole moment. Hydrolysis of 19 followed by alkylation with chloromethyl methyl ether and oxidation with molecular oxygen gave 26 and 27, which on acid hydrolysis gave 4-demethoxyxanthodaunomycinone (29) and 4-demethoxy-7-epixanthodaunomycinone (30). Preliminary biological assays with MCF-7, a human breast cancer cell line, showed that both 29 and 30 were weakly active while daunomycinonc, the aglycone of 2, showed no activity under similar conditions.

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