Total syntheses of the slime mold alkaloid arcyriacyanin A

被引：52

作者：

Brenner, M ^{[1
]}

Mayer, G ^{[1
]}

Terpin, A ^{[1
]}

Steglich, W ^{[1
]}

机构：

[1] UNIV MUNICH,INST ORGAN CHEM,D-80333 MUNICH,GERMANY

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 1997年 / 3卷 / 01期

关键词：

alkaloids; Heck reactions; heterocycles; indoles; total syntheses;

D O I：

10.1002/chem.19970030112

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Arcyriacyanin A (1) has been synthesized by three different routes. In the first synthesis the bisbromomagnesium salt of 2,4'-biindole (5) was treated with dibromomaleimide (6) to yield arcyriacyanin A (1). The second approach used an intramolecular Heck reaction for the cyclization of a 4-(triflyloxy)arcyriarubin 8 to N-methylarcyriacyanin A (2), Thirdly, compound 2 was obtained by a domino Heck reaction between 3-bromo-4-[1-(tert-butoxycarbonyl)indol-3-yl]-1-methylmaleimide (9) and 4-bromoindole (10). The N-methyl derivative 2 could be transformed into arcyriacyanin A (1) by standard methods.

引用

页码：70 / 74

页数：5

共 38 条

[11] PALLADIUM-CATALYZED CARBONYLATION OF ARYL TRIFLATES - SYNTHESIS OF ARENECARBOXYLIC ACID-DERIVATIVES FROM PHENOLS [J].