Devlin A Sloan, Bois J Du
Department of Chemistry, Stanford University, Stanford, CA 94305-5080, USA.
Chem Sci. 2013 Mar 1;4(3):1059-1063. doi: 10.1039/C2SC21723F.
Pentacyclic analogues of the potent voltage-gated sodium ion channel agonist batrachotoxin can be accessed through an intermediate furan by exploiting Diels-Alder cycloaddition reactions with ring-strained dienophiles. The use of 3-bromofuran as a 1,2-dianion equivalent, the application of carbamate reductive N-alkylation for homomorpholine ring assembly, and the demonstration of CsF as an effective reagent for generating benzyne, cyclohexyne, and related dienophiles underscore this work.
强效电压门控钠离子通道激动剂箭毒蛙毒素的五环类似物可通过利用与环应变亲双烯体的狄尔斯-阿尔德环加成反应,经由中间体呋喃来合成。使用3-溴呋喃作为1,2-双负离子等价物、应用氨基甲酸酯还原N-烷基化反应来构建高吗啉环,以及证明氟化铯是生成苯炔、环己炔及相关亲双烯体的有效试剂,这些都突出了这项工作。