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通过串联[2+2]环加成/反曼尼希断裂/曼尼希反应实现(±)-Myrioneurinol 的简洁合成。

Concise Synthesis of (±)-Myrioneurinol Enabled by Sequential [2+2] Cycloaddition/Retro-Mannich Fragmentation/Mannich Reaction.

机构信息

Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry & Chemical Engineering, South China University of Technology, Wushan Road-381, Guangzhou, 510641, P.R. China.

State Key Laboratory of Chemical Oncogenomics, Guangdong Provincial Key Laboratory of Chemical Genomics, Peking University, Shenzhen Graduate School, Shenzhen, Guangdong, 518055, P.R. China.

出版信息

Angew Chem Int Ed Engl. 2022 Jun 27;61(26):e202200085. doi: 10.1002/anie.202200085. Epub 2022 Mar 30.

Abstract

A concise total synthesis of (±)-myrioneurinol has been achieved in 14 steps. An efficient AgSbF /t-BuCl-catalyzed intramolecular [2+2] cycloaddition reaction of the alkynone-tethered enamine was developed to prepare the highly strained cyclobutene. It was used in combination with a subsequent retro-Mannich fragmentation/Mannich reaction to efficiently construct the tricyclic core of myrioneurinol.

摘要

已通过 14 步反应实现了(±)-myrioneurinol 的简洁全合成。开发了一种有效的 AgSbF/t-BuCl 催化的炔酮-连接的烯胺的分子内[2+2]环加成反应,以制备高度应变的环丁烯。该方法与随后的逆-Mannich 断裂/Mannich 反应相结合,有效地构建了 myrioneurinol 的三环核心。

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