Aromatic substitution in dehydroabietane derivatives. Syntheses of the phenolic dehydroabietane series.
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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).
収録刊行物
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- CHEMICAL & PHARMACEUTICAL BULLETIN
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CHEMICAL & PHARMACEUTICAL BULLETIN 29 (6), 1567-1579, 1981
公益社団法人 日本薬学会
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詳細情報
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- CRID
- 1390282679144448256
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- NII論文ID
- 110003633865
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- NII書誌ID
- AA00602100
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- COI
- 1:CAS:528:DyaL3MXlvVOnt7o%3D
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- ISSN
- 13475223
- 00092363
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- 本文言語コード
- en
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- データソース種別
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- JaLC
- Crossref
- CiNii Articles
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- 抄録ライセンスフラグ
- 使用不可