Notoamides F、I、R 和 Sclerotiamide 的全合成。
Total Synthesis of Notoamides F, I, and R and Sclerotiamide.
机构信息
Key Laboratory of Organofluorine Chemistry and Collaborative Innovation Center of Chemistry for Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P.R. China.
School of Chemical Engineering, Ningbo University of Technology, 89 Cuibai Road, Ningbo, 315016, P.R. China.
出版信息
Angew Chem Int Ed Engl. 2016 Aug 22;55(35):10435-8. doi: 10.1002/anie.201604754. Epub 2016 Jul 22.
The total synthesis of the natural indole alkaloids (+)-notoamide F, I, and R and (-)-sclerotiamide is described. The four heptacyclic compounds were synthesized in 10-12 steps in a convergent and highly stereoselective manner from the readily available Seebach acetal. Key steps of the synthesis include a stereoselective oxidative aza-Prins cyclization to construct the bicyclo[2.2.2]diazaoctane, and a cobalt-catalyzed radical cycloisomerization to create the cyclohexenyl ring.
本文描述了天然吲哚生物碱 (+)-notoamide F、I 和 R 以及 (-)-sclerotiamide 的全合成。这四个七元杂环化合物是通过 Seebach 缩醛从易得的原料出发，以 10-12 步的方式，以汇聚和高度立体选择性的方式合成的。合成的关键步骤包括立体选择性的氧化氮杂-Prins 环化来构建双环[2.2.2]二氮杂辛烷，以及钴催化的自由基环异构化来构建环己烯环。
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