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

Rys Véronique | Zendy; Couture Axel | Zendy; Deniau Eric | Zendy; Grandclaudon Pierre | Zendy

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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

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)

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