Unified Approach to Prenylated Indole Alkaloids: Total Syntheses of (-)-17-Hydroxy-Citrinalin B, (+)-Stephacidin A, and (+)-Notoamide I.
Unified Approach to Prenylated Indole Alkaloids: Total Syntheses of (-)-17-Hydroxy-Citrinalin B, (+)-Stephacidin A, and (+)-Notoamide I.
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DOI：
10.1039/c5sc01977j
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发表时间：
2015-08-01
期刊：
影响因子：
8.4
通讯作者：
Sarpong R
中科院分区：
文献类型：
--
作者：
Mercado-Marin EV;Sarpong R
据报道，第一个策略提供了具有特征性双环[2.2.2]二氮杂辛烷以及缺乏该结构基序的反异戊二烯化吲哚生物碱。提出了异戊二烯化吲哚生物碱同系物合成的统一策略。该策略首次合成了天然产物 (–)-17-羟基-柠檬醛 B 以及 (+)-千花菌素 A 和 (+)-诺托酰胺 I。烯醇化物加成到原位生成的异氰酸酯中，用于形成关键的双环[2.2.2]二氮杂辛烷部分，并以这种方式通过合成连接异戊二烯化吲哚生物碱的两个结构类别。
The first strategy that provides reverse-prenylated indole alkaloids that bear a characteristic bicyclo[2.2.2]diazaoctane as well as those that lack this structural motif is reported. A unified strategy for the synthesis of congeners of the prenylated indole alkaloids is presented. This strategy has yielded the first synthesis of the natural product (–)-17-hydroxy-citrinalin B as well as syntheses of (+)-stephacidin A and (+)-notoamide I. An enolate addition to an in situ generated isocyanate was utilized in forging a key bicyclo[2.2.2]diazaoctane moiety, and in this way connected the two structural classes of the prenylated indole alkaloids through synthesis.