Miller Kenneth A, Welch Timothy R, Greshock Thomas J, Ding Yousong, Sherman David H, Williams Robert M
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523-1872, USA.
J Org Chem. 2008 Apr 18;73(8):3116-9. doi: 10.1021/jo800116y. Epub 2008 Mar 18.
The biomimetic total syntheses of both malbrancheamide and malbrancheamide B are reported. The synthesis of the two monochloro species enabled the structure of malbrancheamide B to be unambiguously assigned. The syntheses each feature an intramolecular Diels-Alder reaction of a 5-hydroxypyrazin-2(1H)-one to construct the bicyclo[2.2.2]diazaoctane core, which has also been proposed as the biosynthetic route to these compounds.
报道了麦氏酰胺和麦氏酰胺B的仿生全合成。两种单氯化合物的合成使得麦氏酰胺B的结构得以明确确定。每一种合成方法都以5-羟基吡嗪-2(1H)-酮的分子内狄尔斯-阿尔德反应为特征，构建双环[2.2.2]二氮杂辛烷核心，这也被认为是这些化合物的生物合成途径。
