Studies on the Terpenoids and Related Alicyclic Compounds. XXXIV. Total Synthesis of Highly Oxygenated Furanoeremophilanes : (±)-1β, 10β-Epoxyfuranoeremophilane-6,9-dione and (±)-Epoxydecompositin
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概要
- 論文の詳細を見る
A total synthesis of (±)-1β, 10β-epoxyfuranoeremophilane-6,9-dione (8) and (±)-epoxydecompositin (25) is described. The key step in this synthesis is the epoxidation of the allylic alcohol (10). A model experiment was carried out using the readily available diketone (7) to give the desired 1β, 10β-epoxide (16) stereoselectively in good overall yields. The diketone (17) was reduced with NaBH_4 to give the 9β, 10α-diol (18a), which was treated with Ac_2O then dehydrated with SOCl_2 to give the unexpected rearranged product 19a. The 9-hydroxyl group of 18a was protected with a trimethylsilyl group to give 20. The desired allylic alcohol (10) was derived from 20 via 21a in excellent yield. Epoxidation followed by MnO_2 oxidation of 10 gave (±)-8. NaBH_4 reduction of (±)-8 followed by acetylation with Ac_2O gave (±)-25
- 社団法人日本薬学会の論文
- 1984-09-25
著者
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佐藤 毅
東京理科大学理学部
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佐藤 毅
Faculty of Pharmaceutical Sciences, Science University of Tokyo
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山川 浩司
Faculty of Pharmaceutical Sciences, Science University of Tokyo
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飯田 敏明
Faculty of Pharmaceutical Sciences, Science University of Tokyo
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中島 範行
Faculty of Pharmaceutical Sciences, Science University of Tokyo
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岩崎 正志
Faculty of Pharmaceutical Sciences, Science University of Tokyo
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山川 浩司
Faculty Of Pharmaceutical Sciences Science University Of Tokyo
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中島 範行
Faculty Of Pharmaceutical Sciences Science University Of Tokyo
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山川 浩司
東京理大
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岩崎 正志
Faculty Of Pharmaceutical Sciences Science University Of Tokyo
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Satoh T
Department Of Applied Chemistry Faculty Of Engineering Osaka University
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Sato Toshiyuki
Yamagata Research Institute Of Technology
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飯田 敏明
Faculty Of Pharmaceutical Sciences Science University Of Tokyo
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