Springer Online Journal Archives 1860-2000
Chemistry and Pharmacology
Abstract The interactions with KOH in boiling diethyleneglycol of 3β,28-dimethoxy- and 3β-acetoxy-28-methoxy-18,19-secolupane-18,19-diones have been studied. In the first case, 3β-methoxy-19,20,21,22,29,30-hexanor-18,19-seco(17βH)lupan-18-one and the corresponding 18-ol were isolated from the mixture of products, and in the second case 3β-hydroxy-19,20,21,22,29,30-hexanor-18,19-seco(17βH)lupan-18-one — which was also obtained by an analogous reaction from 3β-acetoxy-18,19-secolupan-18,19-dione — and 3β-hydroxy-19,20,21,22,28,29,30-heptanor-18,19-secolupan-18-one. Thus, it has been found that in this case the retro-Michael reaction is accompanied by 28-demethoxylation and partially by 28-demethoxy-methylation.
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