著者

末宗 洋 小田 晃造 佐伯 清太郎 酒井 浄

出版者

公益社団法人日本薬学会

雑誌

Chemical & pharmaceutical bulletin (ISSN:00092363)

巻号頁・発行日

vol.36, no.1, pp.172-177, 1988-01-25

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This paper describes the conversions of (-)-limonene to four nepetalactones (1,2,ent-3 and 4) in a stereocontrolled manner. The cis-3,4-disubstituted cyclopentanone (5) obtained from (-)-limonene via Rh(I)-catalyzed cyclization of the 4-pentenal, could be converted to the bicyclo[3.3.0]octenone (6). After the stereoselective conversion of 6 into the diastereomeric isomers of the ketones (8 and 16), a sequence of reactions involving the silyl enol ethers (18 and 19), ozonolysis, and subsequent lactonization afforded the target molecules.