How to ‘Cope’ with the Prenylation of the Indole C4 Position

Abstract

Evidence supporting an enzyme-catalyzed [3,3]-sigmatropic rearrangement of the dimethallylltryptophan synthase is highlighted. A bioinspired system is discussed, by which the chemical feasibility of Cope rearrangement to the 4-position of the indole nucleus was accomplished. Furthermore, synthesis of the tricyclic benzo[cd]indole core of welwitindolinones and dragmacidine E is presented.

Key words

biomimetic synthesis - biosynthesis - pericyclic reaction - enzymes - alkaloids

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