Abstract
Reactions of methyl dehydroabietate derivatives having electron-donating group at aromatic C-ring with aluminum chloride were examined. It became clear that the reaction proceeded through isomerisation of 9, 10-bond and/or deisopropylation and the direction of the reaction is affected by the substituent at the aromatic C-ring. For instance, the reaction of 12-hydroxy ester (7) proceeded through both routes while 14-hydroxy ester (19) was selectively deisopropylated. Interconversion between cis- and trans-stereoisomers of deisopropyl ester (e.g., 10h9) was observed and the former is predominant in the equilibrium.
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