G. Lai et Wk. Anderson, Synthesis of novel indole analogues of mycophenolic acid as potential antineoplastic agents, TETRAHEDRON, 56(17), 2000, pp. 2583-2590
The expedient synthesis of three novel indole analogues, 2a-c, of mycopheno
lic acid is described, which involved as the key steps both the Et2O . BF3
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 oxid
ation-aminolysis or oxidation-methoxylation. The synthetic approach describ
ed possesses general usefulness. The analogue 2b showed significant, reprod
ucible antitumor activity. (C) 2000 Elsevier Science Ltd. All rights reserv
ed.