Benzo[7,8]indolizinoquinoline scaffolds based on Mg(ClO4)2-promoted regiospecific imide reduction and π-cyclization of N-acyliminium species. Analogues of the topo-1 poison rosettacin and 22-hydroxyacuminatine alkaloids

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Hamid, Abdulkareem | Souizi, Abdelaziz | Lawson, Ata Martin | Othman, Mohamed | Ghinet, Alina | Rigo, Benoît | Daïch, Adam

Edité par HAL CCSD ; Elsevier

International audience. A general five-step synthesis of a short library of benzo[7,8]indolizinoquinolinine analogues of the topoisomerase-1 (topo-1) poison rosettacin and 22-hydroxyacuminatine alkaloids from DMAD and ortho-ketoanilines is reported. This consists on successively, the tandem aza-Michael addition/cyclodehydration, the hydrolysis of the resulting diesters into corresponding o-dicarboxylic acids, and the tandem intermolecular amidation/cyclodehydration into N-substituted imides. The regioselective reduction of one imide carbonyl into corresponding α-hydroxy lactams promoted by a Lewis acid Mg(ClO4)2 was followed ultimately with TFA-promoted π-cationic cyclization via stable N-acyliminiums species as an important key step.

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