Abstract
The expedient synthesis of three novel indole analogues, 2a– c, of mycophenolic acid is described, which involved as the key steps both the Et 2O·BF 3 catalyzed amino-Claisen rearrangement of N-allylindoline to 7-allylindoline and the ortho ester Claisen rearrangement of the allylic alcohol 12 to the methyl ester 14. The installation of the substituents at the C-3 position in 2b and 2c was accomplished via Vilsmeier formylation and subsequent oxidation–aminolysis or oxidation–methoxylation. The synthetic approach described possesses general usefulness. The analogue 2b showed significant, reproducible antitumor activity.
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