10 Benzeneseleninic Anhydrideによる新らしい核間水酸化反応と天然物合成への応用 : (±)-Decompositinおよび関連化合物の全合成
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概要
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Stereochemical study on the angular hydroxylation of polycyclic ketones using benzeneseleninic anhydride and its application to the total synthesis of furanoeremophilanes are described. Introduction of a hydroxyl group to the tertiary carbon of simple ketones (8-10), furanoeremophilane-type ketones (16-20) was accomplished by the use of benzeneseleninic anhydride. 10β-Hydroxy compounds were obtained in the case of 16-18. 10α-Hydroxy compounds were obtained in the case of 19 and 20. In the hydroxylation reaction of polycyclic ketones using benzeneseleninic anhydride, the results suggest that the thermodynamically more stable product was usually produced as the major products. Deketalization of 10α-hydroxy compound 22b followed by acetylation gave triketo-acetate (37). Thioketalization of 37 followed by treatment with K_2CO_3 afforded 39b. Desulfurization of 39b gave a mixture of 40 and dehydro product (41) in 90% yield. The mixture was reduced with Pd-C to give 40 quantitatively. Dehydration of 40 with SOCl_2 followed by reduction with NaBH_4 gave (±)-43a. (±)-Adenostylone (43b), (±)-decompositin (4), and (±)-tetrahydro-decompositin (44) were synthesized from (±)-43a in a good yield, respectively. 3β-Propionyloxy compound (45b), which was derived from 29, was treated with benzeneseleninic anhydride to give 10β-hydroxy compound (46a) and 10α-hydroxy compound (46b). (±)-3β,6β-Dipropionyloxy-euryopsin-9-one (48b) was synthesized from the hydroxy compound (46b) in three steps.
- 天然有機化合物討論会の論文
- 1980-09-10
著者
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佐藤 毅
東京理科大学理学部
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滝田 敏
Faculty of Pharmaceutical Sciences, Science University of Tokyo
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滝田 敏
Faculty Of Pharmaceutical Sciences Science University Of Tokyo
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山川 浩司
東京理大
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佐藤 毅
東理大・薬
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滝田 敏
東理大・薬
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田村 伸彦
東理大・薬
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山川 浩司
東理大・薬
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田村 伸彦
東北大・薬
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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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