A NEW CYCLOPENTANOL AS A SIDE PRODUCT IN THE REDUCTION OF THE CHALCONE : ŞALKONUN REDÜKSİYONUNDA BİR YAN ÜRÜN OLARAK YENİ BİR SİKLOPENTANOL

As a part of an ongoing study on the synthesis of 1,3-diphenylpropanones, as key intermediates in the total synthesis of 11,12-dihydro-10,5-(iminomethano)-5H,10H-dibenzo[a,d]cyclooctenes with potential Central Nervous System activity, 3-(3,4-dimethoxyphenyl)-l-(3-tolyl)-2-propenone is obtained by the Claisen-Schmidt reaction of 3,4-dimethoxybenzaldehyde and 3-methylacetophenone. At the second step, the reduction of the olefinic bond of chalcone was attempted by using Zn/acetic acid. Although the desired saturated ketone was obtained during this reduction, the major product was a new cyclopentanol, formed by cyclodimerization. The structure and the stereochemistry of this new compound was elucidated by ID and 2D NMR analyses.