Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, Indiana 47405, United States.
J Am Chem Soc. 2020 Mar 18;142(11):5002-5006. doi: 10.1021/jacs.0c00359. Epub 2020 Mar 9.
The first enantioselective synthesis of (-)-cajanusine is presented. Key features of the route include a rapid synthesis of the [4.2.0]bicyclooctane core by an enantioselective isomerization/stereoselective [2+2]-cycloaddition strategy as well as prominent use of catalytic methods for bond construction. The evolution of the approach is also presented that highlights unexpected roadblocks and how novel solutions were developed.
首次呈现了 (-)-卡京宁的对映选择性全合成。该路线的关键特点包括通过对映选择性异构化/立体选择性[2+2]-环加成策略快速合成[4.2.0]二环辛烷核心,以及显著使用催化方法进行键合构建。还呈现了该方法的演变过程,突出了意想不到的障碍以及如何开发新的解决方案。