通过多米诺迈克尔/曼尼希/N-烷基化反应构建四氢咔唑骨架的方法：(-)-阿朴斯底明碱、(-)-塔伯色林碱和(-)-长春质碱的简洁全合成。
Domino Michael/Mannich/N-alkylation route to the tetrahydrocarbazole framework of aspidosperma alkaloids: concise total syntheses of (-)-aspidospermidine, (-)-tabersonine, and (-)-vincadifformine.
机构信息
Department of Chemistry, Temple University , Philadelphia, Pennsylvania 19122, United States.
出版信息
J Am Chem Soc. 2013 Sep 11;135(36):13334-7. doi: 10.1021/ja408114u. Epub 2013 Aug 27.
We report a novel, asymmetric domino Michael/Mannich/N-alkylation sequence for the rapid assembly of the tetrahydrocarbazole framework of Aspidosperma alkaloids. This method was utilized in the concise total syntheses of classical targets (-)-aspidospermidine, (-)-tabersonine, and (-)-vincadifformine in 10 or 11 steps. Additional key steps include ring-closing metathesis to prepare the D-ring and Bosch-Rubiralta spirocyclization to prepare the C-ring.
我们报告了一种新颖的、不对称的多米诺迈克尔/曼尼希/N-烷基化序列，用于快速构建阿皮斯多玛烷生物碱的四氢咔唑骨架。该方法被用于简洁的全合成经典目标物（-）-阿皮斯多麦定、（-）-塔博萨定和（-）-长春多卡辛，总步数为 10 步或 11 步。其他关键步骤包括闭环复分解反应制备 D 环和 Bosch-Rubiralta 螺环化反应制备 C 环。
Zotero 插件