Synthesis of Indole-, Benzo[b]thiophene-, and Benzo[b]selenophene-Based Analogues of the Resveratrol Dimers Viniferifuran and (±)-Dehydroampelopsin B
Synthesis of Indole-, Benzo[b]thiophene-, and Benzo[b]selenophene-Based Analogues of the Resveratrol Dimers Viniferifuran and (±)-Dehydroampelopsin B
复制标题
DOI：
10.1021/acs.orglett.8b02638
复制
发表时间：
2018-11-02
期刊：
影响因子：
5.2
通讯作者：
Elofsson, Mikael
中科院分区：
文献类型：
--
作者：
Krzyzanowski, Adrian;Saleeb, Michael;Elofsson, Mikael
提出了一种方便的合成策略，以获得基于吲哚，苯并[B]噻吩和苯并[B]硒杂环核的viniferifuran和（+/-）-脱氢蛇葡萄素B类似物。所述合成中使用的关键转化包括Sonogashira偶联、Cacchi和炔亲电环化、Horner-Wadsworth-Emmons（HWE）反应、化学选择性Suzuki-Miyaura偶联和酸促进的分子内环化以形成（+/-）-脱氢蛇葡萄素B的七元环。
A convenient synthetic strategy to obtain viniferifuran and (+/-)-dehydroampelopsin B analogues based on the heterocyclic cores of indole, benzo[b]thiophene, and benzo[b]selenophene is presented. The key transformations utilized in the described syntheses include Sonogashira couplings, Cacchi and alkyne electrophilic cyclizations, Horner-Wadsworth-Emmons (HWE) reaction, chemoselective Suzuki-Miyaura couplings, and acid-promoted intramolecular cyclization to form the sevenmembered ring of (+/-)-dehydroampelopsin B.