Nodwell Matt, Riffell Jenna L, Roberge Michel, Andersen Raymond J
Departments of Chemistry and Earth & Ocean Sciences, University of British Columbia, Vancouver, B.C., Canada.
Org Lett. 2008 Mar 20;10(6):1051-4. doi: 10.1021/ol7030284. Epub 2008 Feb 16.
Antimitotic analogs of the microtubule stabilizing sponge alkaloid ceratamine A (1) have been synthesized starting from tribromoimidazole. A key step in the synthesis is the formation of the azepine ring via an intramolecular Buchwald coupling between a vinyl bromide and a N-methyl amide. This represents the first synthesis of a fully unsaturated imidazo[4,5,d]azepine. NMR data obtained for the synthetic ceratamine analogs has provided support for the structure assigned to the natural product.
已从三溴咪唑开始合成了微管稳定海绵生物碱角胺A（1）的抗有丝分裂类似物。合成中的关键步骤是通过乙烯基溴与N-甲基酰胺之间的分子内布赫瓦尔德偶联形成氮杂环庚三烯环。这代表了完全不饱和咪唑并[4,5,d]氮杂环庚三烯的首次合成。为合成的角胺类似物获得的核磁共振数据为天然产物的指定结构提供了支持。
