Chemical Transformation of Terpenoids. V. Acidic Conversions of 10-Hydroxygeraniol and 10-Hydroxynerol Derivatives Leading to Cyclic Monoterpenoids
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概要
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Acid treatment of 1-O-acetyl-10-hydroxygeraniol (5a), 1-O-methyl-10-hydroxygeraniol (5b), 1-O-acetyl-10-hydroxynerol (6a), and 1-O-methyl-10-hydroxynerol (6b) was investigated under various conditions. It was found that treatment of 5a and 6a with HCOOH gave menth-1-ene-8,9-diol (7), while treatment of 5a, 5b, 6a, or 6b with BF_3-etherate in CH_2Cl_2 furnished two menthofuran-type compounds (9,10) and two bicyclo[3.2.1]oct-2-ene derivatives (17,24). Both 9 and 10 were successfully converted to menthofuran (16) and 17 was converted to a bicyclo[3.2.1]octenone derivative (23) which was a key intermediate for a synthesis of juvabione (27).
- 公益社団法人日本薬学会の論文
- 1983-08-25
著者
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渋谷 博孝
Faculty of Pharmaceutical Sciences, Osaka University
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辻井 伸治
Faculty of Pharmaceutical Sciences, Osaka University
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西川(宮本) 富美子
Faculty Of Pharmaceutical Sciences Osaka University
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辻井 伸治
Faculty Of Pharmaceutical Sciences Osaka University
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