CHs ch3VI VII of C(e) and C(g), the relative configurations at these carbon atoms are the same in the Michael adduct VII as in santonin. It is probable that the malonic ester substituent at C<6) and the angular methyl group at C(9) are cis in the Michael adduct (malonic ester group equatorial) because in the very closely analogous addition of malonic ester to cholesta-3,5-diene-7-one (VIII) the malonic ester substituent assumes the equatorial (ß) orientation, cis to the angular methyl group.10-12 The equatorial arrangement is the more stable one and would to assign formula IX to ß-santonin and formula X to artemisin.
IX XNote added January 8.-Since the submission of this manuscript for publication, R. B. Woodward and P. Yates [Chem. and Ind., 1319 (1954)] have proposed structure I for santonin on the basis of arguments similar to those presented herein.
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