Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, USA.
J Am Chem Soc. 2012 Jan 25;134(3):1396-9. doi: 10.1021/ja210837b. Epub 2012 Jan 11.
We report the total synthesis of (-)-N-methylwelwitindolinone C isonitrile, in addition to the total syntheses of the 3-hydroxylated welwitindolinones. Our routes to these elusive natural products feature the strategic use of a deuterium kinetic isotope effect to improve the efficiency of a late-stage nitrene insertion reaction. We also provide a computational prediction for the stereochemical configuration at C3 of the hydroxylated welwitindolinones, which was confirmed by experimental studies.
我们报告了(-)-N-甲基威尔维蒂宁酮 C 异腈的全合成,此外还完成了 3-羟基威尔维蒂宁酮的全合成。我们这些难以捉摸的天然产物的路线的特点是战略性地利用氘动力学同位素效应来提高晚期氮宾插入反应的效率。我们还对羟基威尔维蒂宁酮 C3 处的立体化学构型进行了计算预测,该预测通过实验研究得到了证实。