Total syntheses of five indole alkaloids from the marine bryozoan Flustra foliacea
Total syntheses of five indole alkaloids from the marine bryozoan Flustra foliacea
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DOI：
10.1021/jo0012647
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发表时间：
2001-02-23
影响因子：
3.6
通讯作者：
Joseph-Nathan, P
中科院分区：
文献类型：
--
作者：
Morales-Ríos, MS;Suárez-Castillo, OR;Joseph-Nathan, P
概述了一种通用、高效和概念上新的海洋衍生吲哚生物碱的全合成方法，包括(+/-)-氟杂环胺A(I)和B(2)、(+/-)-氟杂环丁二胺A(3)和B(4)以及(+/-)-脱溴氟杂环丁胺B(5)。合成的关键步骤是将一种由戊二烯基溴衍生的有机镁物种与2-羟基吲哚进行共轭加成。以2-羟基吲哚为原料，分五步合成了化合物1、2和5，总收率分别为23%、17%和16%，而以2-羟基吲哚为原料，仅经四步合成了化合物3和4，总收率分别为24%和18%。
A general, efficient, and conceptually new approach to the total syntheses of marine-derived indole alkaloids, including (+/-)-flustramines A (I) and B (2), (+/-)-flustramides A (3) and B (4), and (+/-)-debromoflustramine B (5), is outlined. The key step in the syntheses involves the conjugated addition of an organomagnesium species derived from prenyl bromide to 2-hydroxyindolenines. Compounds 1. 2, and 5 have been synthesized in five steps with 23%, 17%, and 16% overall yield, respectively, whereas flustramides 3 and 4 have been synthesized in only four steps with 24% and 18% overall yield, respectively, on the basis of 2-hydroxyindolenines.