环状丙二烯方法合成曼扎明生物碱凯拉马芬丁 B。
Cyclic Allene Approach to the Manzamine Alkaloid Keramaphidin B.
机构信息
Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, United States.
出版信息
Org Lett. 2023 Aug 4;25(30):5553-5557. doi: 10.1021/acs.orglett.3c01489. Epub 2023 Jun 30.
Abstract
We report an approach to the core of the manzamine alkaloid keramaphidin B that relies on the strain-promoted cycloaddition of an azacyclic allene with a pyrone trapping partner. The cycloaddition is tolerant of nitrile and primary amide functional groups and can be complemented with a subsequent retro-Diels-Alder step. These efforts demonstrate that strained cyclic allenes can be used to build significant structural complexity and should encourage further studies of these fleeting intermediates.
摘要
我们报告了一种针对曼扎明生物碱 keramaphidin B 核心的方法，该方法依赖于应变促进的氮杂环丙烯与吡喃酮捕获试剂的环加成。该环加成反应对腈和伯酰胺官能团具有耐受性，并且可以与随后的逆狄尔斯-阿尔德反应步骤相补充。这些努力表明，应变环状丙烯可以用于构建重要的结构复杂性，并且应该鼓励对这些短暂中间体的进一步研究。
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