A Short Total Synthesis of the Alkaloids Piperolactam C, Goniopedaline, and Stigmalactam

Abstract

Abstract The total synthesis of the polyalkoxylated alkaloids piperolactam C, goniopedaline and stigmalactam by combinatorial metalation/cyclization strategies has been achieved. The synthetic route involved the preliminary construction of the polyalkoxylated isoindolinone template by Parham’s technique. Benzylic lactam deprotonation allowed connection of a hydroxybenzyl appendage, and the synthesis of the target natural products was completed by subsequent E1cB elimination, radical cyclization and final deprotection. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)