19 エレモフィラン類セスキテルペンの合成研究
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概要
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Syntheses of (±)-liguralone (2) and some eremophilanes by the Diels-Alder reaction of 3-ethoxy-1,3-pentadiene (5) and furanoquinone (6) or 3-carendione (20), respectively, were investigated. 1) Total Synthesis of (±)-Liguralone (2) The Diels-Alder reaction of the diene (5) and quinone (6) gave an adduct (7) regioselectively, which was easily epimerized to epimer (8). Reduction of (8) with NaBH_4 gave epimeric alcohol (9) and (10), whose dehydration afforded cis-dimethyl compound (12) in low yield. Catalytic reduction of (12) afforded diketone (16) which was identified with authentic (16). Conversion of (16) into (+)-liguralone (2) had been completed by Naya et al. The adduct (7) and (8) were converted into triketone (19), which was identified with Bohlmann's compound. 2) Synthesis of Eremophilanes by the Diels-Alder Reaction of Diene (5) and Carendione (20) The Diels-Alder reaction of diene (5) and carendione (20) afforded the adduct (20) and (22) in a ratio of 1: 3. (22) was easily epimerized to triketone (23) with acid. Reduction of ketal (24) with NaBH_4 gave 9α-OH (25) and 9β-OH (26) in a ratio of 7: 3. Treatment of (25) and (26) with TsCl in pyridine yielded eremophilane skeletal compound (29). Moreover, conversion of diol (30) and (31) into eremophilane type diene (32) was carried out. The base-induced transannular hydride shift was found between ketol (25) and (34). A novel hydride rearrangement was confirmed by deuterated compound (35) and (36).
- 天然有機化合物討論会の論文
- 1976-09-20
著者
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佐藤 毅
東京理科大学理学部
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坂口 礼司
Faculty of Pharmaceutical Sciences, Science University of Tokyo
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坂口 礼司
Faculty Of Pharmaceutical Sciences Science University Of Tokyo
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山川 浩司
東京理大・薬
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坂口 礼司
東京理大・薬
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佐藤 毅
東京理大・薬
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山川 浩司
東京理大
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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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