Studies of the selective O-alkylation and dealkylation of flavonoids. XIX. A convenient method for synthesizing 3,5,6,7,8-pentaoxygenated flavones

DOI: 10.1248/cpb.43.2054

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Chemical and Pharmaceutical Bulletin p. 2054 - 2063 (1995)

Update date:2022-08-04

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Authors:

Horie Horie

Kawamura

Yamamoto

Yamashita

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Article abstract of DOI:10.1248/cpb.43.2054

The methoxymethyl ethers of 6-hydroxy-5,7,8-trimethoxyflavones, which were derived from 2',5'dihydroxy-3',4',6'-trimethoxyacetophenone, were oxidized with dimethyldioxirane to give the corresponding 3-hydroxyflavones. Selective O-alkylation and dealkylation of the 3-hydroxyflavones were examined and a convenient method for synthesizing the following ten kinds of 3,5,6,7,8- pentaoxygenated flavones was established: 3-hydroxy-5,6,7,8- tetramethoxyflavones, 3,5-dihydroxy-6,7,8-trimethoxyflavones, 3,6-dihydroxy- 5,7,8-trimethoxyflavones, 3,5,6-trihydroxy-7,8-dimethoxyflavones, 3,5,6,7- tetrahydroxy-8-methoxyflavones, and their 3-methyl ethers. Furthermore, 3,5,8-trihydroxy-4',6,7-trimethoxyflavone, 3,8-dihydroxy-4',5,6,7- tetramethoxyflavone, and 5,8-dihydroxy-3,6,7-trimethoxyflavones were similarly synthesized and their spectral properties were examined. Additionally, the proposed structures of three natural flavones were revised.

Full text of DOI:10.1248/cpb.43.2054

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