Aromatic Substitution in Dehydroabietane Derivatives. : Syntheses of the Phenolic Dehydroabietane Series
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概要
- 論文の詳細を見る
In order to investigate the relationship between the position of the hydroxy group on the aromatic C-ring of dehydroabietane and the cleavage pattern upon ozonolysis, phenolic dehydroabietane derivatives having a hydroxyl group on every possible position (11-, 12-, 13-, and 14-positions) were synthesized from dehydroabietic acid (2). Friedel-Crafts acetylation of dehydroabietane (7) derived from 2 gave the 12-acetyl compound (8), which was converted to the 12-hydroxy compound (ferruginol, 10) and 11,12-dihydroxy dehydroabietane (14). On the other hand, nitration of 7-oxo dehydroabietane (25) afforded a mixture of the 14-nitro-7-oxo compound (26) and the 13-nitro-7-oxo compound (27) in ca. 1 : 1 ratio. The former (26) was converted into 14-hydroxy dehydroabietane (32) and the latter (27) was led to both the 13-hydroxy compound (37) and the 13,14-dihydroxy compound (47).
- 公益社団法人日本薬学会の論文
- 1981-06-25
著者
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秋田 弘幸
理化学研究所
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秋田 弘幸
Rikagaku Kenkyusho (The Institute of Physical and Chemical Research)
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大石 武
Rikagaku Kenkyusho (The Institute of Physical and Chemical Research)
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