Abstract
Addition of chlorine to the double bond of α-santonin derivatives such as santonin chlorohydrin (4) santonin α-epoxide (5), and 5-chloro-4-methoxysatonin (6) produced new chloro-santonins (13, 14, 16, respectively). So far, only trans addition of chlorine to the 1, 2-double bond of santonin has been known, but from the configuration of these products, it wa clear that cis addition had occuured. 'Santonin dichloride' (2), and 2-chlorosantonin (3), were chloromethoxylated and chloro-hydroxylated to produce tetrasubstituted compounds (9 and 10), and trisubstituted compounds (11 and 12), respectively. Their structure and configuration were determined by interrelating them to known santonin derivatives (2, 3, 4, 5, and 6) and by X-ray analysis of 13.
