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 KHSO₄ 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.