Synthetic Study toward Ecteinascidin 743: Concise Construction of the Diazabicyclo[3.3.1]nonane Skeleton and Assembly of the Pentacyclic Core

Synthetic Study toward Ecteinascidin 743: Concise Construction of the Diazabicyclo[3.3.1]nonane Skeleton and Assembly of the Pentacyclic Core
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DOI:
10.1021/jo100788j
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发表时间:
2010-07-16
影响因子:
3.6
通讯作者:
Takemoto, Yoshiji
Takemoto, Yoshiji
中科院分区:
化学2区
文献类型:
--
作者:
Enomoto, Taro;Yasui, Yoshizumi;Takemoto, Yoshiji

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本文报道了五环胞外杀菌素743的合成。本合成的特点是以金(I)催化的一锅酮酰胺形成、酸促进的烯胺形成和氧化Friedel-Craft环化为关键步骤,简明地构建了双氮双环[3.3.1]壬烷骨架。
Synthesis of the pentacyclic core of ecteinascidin 743 is described. This synthesis features concise construction of the diazabicyclo[3.3.1]nonane skeleton using gold(I)-catalyzed one-pot keto amide formation, acid-promoted enamide formation, and oxidative Friedel-Crafts cyclization as the key steps.