Reduction of β-Ketoalkyl 2-(1-Dimethylaminoethyl)phenyl Sulfoxides : Synthesis of (-)-Matsutakeol
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概要
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Five β-ketoalkyl 2-(1-dimethylaminoethyl)phenyl sulfoxides (2a-e) were prepared by lithiation at the α-methyl hydrogen to the sulfoxide group of N, N-dimethyl-1-(2-methylsulfinylphenyl)ethylamine (1), followed by condensation with esters. The reduction of 2a-e gave two kinds of β-hydroxysulfoxides (3a-e and 4a-e), whose structures were determined by transforming 4a to naturally occurring (-)-matsutakeol. The results on the diastereoselectivity of this reduction and the ^1H-NMR spectral behavior of the α-hydrogens to the sulfoxide group were different from those found in the case of reduction of β-ketoalkyl tolyl sulfoxides.
- 社団法人日本薬学会の論文
- 1992-11-25
著者
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太田 明廣
東京薬科大学薬学部
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太田 明廣
Tokyo College Of Pharmacy
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後藤 美紀子
Tokyo College of Pharmacy
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島崎 眞
Tokyo College of Pharmacy
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市原 紀恵
Tokyo College of Pharmacy
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太田 明広
東京薬大 薬
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