A Total Synthesis of (±)-Warburganal
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概要
- 論文の詳細を見る
A total synthesis of (±)-warburganal has been completed starting from (±)-isodrimenin and other drimane-type compounds. 11,12-Diacetoxy-drim-8-ene (9), which can be readily obtained from the above starting compounds, was converted to the 7-oxo derivative (7). Treatment of 7 with 30% H_2O_2 followed by NH_2NH_2・H_2O promoted reductive opening of the resulting keto epoxide group to afford the trialcohol (11). Selective silylation of the allylic primary alcohol in 11 with tert-butyldimethylsilyl chloride followed by protection of the α-glycol with N, N'-carbonyldiimidazole afforded the carbonate (14). Desilylation of 14 and subsequent oxidation of the allyl alcohol moiety afforded 16. Protection of the aldehyde followed by base-induced deprotection of the glycol afforded 18,which was subjected to Moffatt oxidation to give 19. Treatment of 19 with p-TsOH-acetone afforded (±)-warburganal.
- 公益社団法人日本薬学会の論文
- 1980-07-25
著者
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秋田 弘幸
Riken Institute (The Institute of Physical and Chemical Research)
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中田 忠
The Institute of Physical and Chemical Research (RIKEN)
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大石 武
The Institute of Physical and Chemical Research (Riken)
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秋田 弘幸
The Institute of Physical and Chemical Research (Riken)
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内藤 隆信
The Institute of Physical and Chemical Research (Riken)
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内藤 隆信
The Institute Of Physical And Chemical Research (riken):(present Address) Research Laboratory Kaken
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