Development of a Merged Conjugate Addition/Oxidative Coupling Sequence. Application to the Enantioselective Total Synthesis of Metacycloprodigiosin and Prodigiosin R1
作者:Michael D. Clift、Regan J. Thomson
DOI:10.1021/ja906122g
日期:2009.10.14
reagent with subsequent enolate trapping by a (chloro)silylenol ether. The process was applied to the first enantioselective syntheses of the biologically active pyrrolophane natural products, metacycloprodigiosin and prodigiosin R1.
已开发出一种合并的共轭加成/氧化偶联序列,该序列代表了制备结构多样的吡咯的有效策略。该方法的成功取决于不对称甲硅烷基双烯醇醚中间体的受控氧化偶联,该中间体由格氏试剂的 1,4-加成形成,随后烯醇被(氯)甲硅烷醇醚捕获。该过程被应用于具有生物活性的吡咯烷天然产物、metacycloprodigiosin 和 prodigiosin R1 的第一次对映选择性合成。