How to 'Cope' with the Prenylation of the Indole C4 Position

被引：19

作者：

Schwarzer, Darius D. ^{[1
]}

Gritsch, Philipp J. ^{[1
]}

Gaich, Tanja ^{[1
]}

机构：

[1] Leibniz Univ Hannover, Inst Organ Chem, Dept Chem, D-30167 Hannover, Germany

来源：

SYNLETT | 2013年 / 24卷 / 09期

关键词：

biomimetic synthesis; biosynthesis; pericyclic reaction; enzymes; alkaloids; ERGOT ALKALOID BIOSYNTHESIS; ELECTROPHILIC SUBSTITUTION; CHORISMATE MUTASE; DIMETHYLALLYLTRYPTOPHAN SYNTHASE; TRANSITION-STATE; CATALYZED REARRANGEMENT; WELWITINDOLINONES; ISONITRILE; ECHINULIN; ENZYME;

D O I：

10.1055/s-0032-1318501

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：1025 / 1031

页数：7

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