著者
末宗 洋 丸岡 博 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.34, no.11, pp.4629-4634, 1986-11-25

This paper describes a conversion of (-)-limonen-10-ol to the key intermediate (1) for 11-deoxyprostaglandin. The 3,4-cis-disubstituted cyclopentanone (2), which was easily obtained from (-)-limonen-10-ol in a stereocontrolled fashion by means of Rh(I)-catalyzed cyclization via the 4-pentenal derivative, could be directly converted to the bicyclo[3.3.0]octenone (3) by treatment with KHSO_4 in boiling benzene. Compound 3 with a double bond at the favorable position was converted to 1 by way of fission of the double bond and subsequent modification of substituents on the five-membered ring.