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A Short Total Synthesis of the Alkaloids Piperolactam C, Goniopedaline, and Stigmalactam
Author(s) -
Rys Véronique,
Couture Axel,
Deniau Eric,
Grandclaudon Pierre
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200390177
Subject(s) - chemistry , total synthesis , metalation , deprotonation , stereochemistry , radical cyclization , combinatorial chemistry , organic chemistry , ion
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)