双（环色胺）生物碱的简洁全合成：硫脲催化的一锅法连续迈克尔加成反应。
Concise total syntheses of bis(cyclotryptamine) alkaloids thio-urea catalyzed one-pot sequential Michael addition.
作者信息
Khatua Arindam, Shyamal Pranay, Pal Souvik, Mondal Ayan, Bisai Alakesh
机构信息
Department of Chemistry, IISER Bhopal, Bhopal Bypass Road, Bhopal - 462 066, Madhya Pradesh, India.
Department of Chemistry, IISER Kolkata, Mohanpur Campus, Kalyani, Nadia - 741 246, West Bengal, India.
出版信息
Chem Commun (Camb). 2022 Mar 22;58(24):3929-3932. doi: 10.1039/d2cc01008a.
Naturally occurring bis(cyclotryptamine) alkaloids feature vicinal all-carbon quaternary stereocenters with an elongated labile C-3a-C-3a' Sigma bond with impressive biological activities. In this report, we have developed a thio-urea catalyzed one-pot sequential Michael addition of bis-oxindole onto selenone to access enantioenriched dimeric 2-oxindoles with vicinal quaternary stereogenic centers at the pseudobenzylic position (up to 96% ee and >20 : 1 dr). This strategy has been successfully applied for the total syntheses of either enantiomers of chimonanthine, folicanthine, and calycanthine.
天然存在的双（环色胺）生物碱具有相邻的全碳季碳立体中心，带有一个延长的不稳定C-3a-C-3a'σ键，并具有令人印象深刻的生物活性。在本报告中，我们开发了一种硫脲催化的双吲哚酮一锅法顺序迈克尔加成到硒酮上的方法，以获得在假苄基位置具有相邻季碳立体中心的对映体富集二聚体2-吲哚酮（对映体过量高达96%，非对映体比例>20:1）。该策略已成功应用于腊梅碱、柳叶蜡梅碱和夏腊梅碱对映体的全合成。
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