Kinsman A C, Kerr M A
Department of Chemistry, University of Western Ontario, London, Ontario N6A 5B7, Canada.
Org Lett. 2000 Nov 2;2(22):3517-20. doi: 10.1021/ol0065773.
[reaction: see text] Ultrahigh pressures and catalytic Yb(OTf)(3).2H(2)O were found to mediate Diels-Alder reactions of various electron-deficient dienophiles with 1,3-cyclohexadiene to produce endo-bicyclo[2.2. 2]oct-2-enes in moderate to excellent yield and selectivity. The proposed total synthesis of hapalindole Q based on bicyclo[2.2. 2]oct-2-ene construction by Diels-Alder reaction and subsequent olefin cleavage is outlined. Preliminary results demonstrating the viability of this strategy are presented.
[反应：见正文] 发现超高压和催化量的Yb(OTf)₃·2H₂O可介导各种缺电子亲双烯体与1,3-环己二烯的狄尔斯-阿尔德反应，以中等至优异的产率和选择性生成内型双环[2.2.2]辛-2-烯。概述了基于通过狄尔斯-阿尔德反应构建双环[2.2.2]辛-2-烯并随后进行烯烃裂解的哈帕林多醇Q的拟议全合成。展示了该策略可行性的初步结果。
