震颤二烯醇A和震颤内酯A的对映选择性合成。
Enantioselective syntheses of tremulenediol A and tremulenolide A.
作者信息
Ashfeld Brandon L, Martin Stephen F
机构信息
Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, Texas 78712, USA.
出版信息
Org Lett. 2005 Sep 29;7(20):4535-7. doi: 10.1021/ol051945u.
[reaction: see text] An enantioselective entry to the skeleton of the tremulane sesquiterpenes is described. The approach features a series of efficient transition metal-catalyzed reactions commencing with an enantioselective rhodium(II)-catalyzed intramolecular cyclopropanation followed by a regioselective allylic alkylation and a diastereoselective rhodium(I)-catalyzed [5 + 2] cycloaddition. This strategy was applied to the first enantioselective syntheses of tremulenediol A and tremulenolide A.
[反应：见正文] 本文描述了一种对映选择性构建震颤烷倍半萜骨架的方法。该方法的特点是一系列高效的过渡金属催化反应，起始于对映选择性铑（II）催化的分子内环丙烷化反应，随后是区域选择性烯丙基烷基化反应和非对映选择性铑（I）催化的[5 + 2]环加成反应。该策略应用于震颤二醇A和震颤内酯A的首次对映选择性合成。
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