The Synthesis of 9-Substituted p-Mentha-1,8 (10)-diene Derivatives
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概要
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The chemical conversion of (+)-limonene (1) and (-)-perillyl alcohol (10) into 9-substituted p-mentha-1,8 (10)-diene derivatives is described. The lithiated species of 1 and 10 were easily obtained in good yields, by using sec-butyl lithium in N, N, N', N'-tetramethylethylenediamine. The reaction of the lithiated species (A and B) with various electrophiles was completed within 1-2 h to give 9-substituted p-mentha-1,8 (10)-diene derivatives. The stereochemistry of the chiral center of the starting material was retained in the products. 9-Hydroxy-p-mentha-1,8 (10)-diene (8) was also obtained by another short sequence of steps. Oxidation of the phenylthio derivative (7) gave the sulfoxide (9). Treatment of 9 with trimethyl phosphite afforded 8.
- 公益社団法人日本薬学会の論文
- 1984-11-25
著者
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末宗 洋
Faculty of Pharmaceutical Sciences, Kyushu University
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酒井 浄
Faculty of Pharmaceutical Sciences, Kyushu University
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酒井 浄
Faculty Of Pharmaceutical Sciences Kyushu University
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末宗 洋
九州大学薬学部
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岩崎 源司
Sagami Chemical Research Center
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上野 貢嗣
Faculty Of Pharmaceutical Sciences Kyushu University
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岩崎 源司
Faculty of Pharmaceutical Sciences, Kyushu University
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