Total syntheses of the slime mold alkaloid arcyriacyanin A
Total syntheses of the slime mold alkaloid arcyriacyanin A
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DOI：
10.1002/chem.19970030112
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发表时间：
1997-01-01
影响因子：
4.3
通讯作者：
Steglich, W
中科院分区：
文献类型：
--
作者：
Brenner, M;Mayer, G;Steglich, W
青蒿素A(1)的合成有三条不同的路线。在第一次合成中，2，4‘-联吲哚的双溴镁盐(5)与二溴马来酰亚胺(6)反应得到青蒿素A(1)。第二种方法利用分子内Heck反应将4-(三氟氧基)青蒿素8环化成N-甲基花青素A(2)，第三种方法是通过3-bromo-4-[1-(tert-butoxycarbonyl)indol-3-yl]-1-methylmaleimide(9)和4-溴吲哚(10)的多米诺-Heck反应得到化合物2。N-甲基衍生物2可以用标准方法转化为青蒿素A(1)。
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.