Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, USA.
Org Lett. 2012 Jun 15;14(12):2929-31. doi: 10.1021/ol301092w. Epub 2012 May 31.
An acid-catalyzed intramolecular [4 + 2] cycloaddition of a non-natural bisabolene is reported. The key cyclocondensation was developed to access cyclic sesquiterpenes from linear phenolic precursors by generating a reactive o-quinone methide intermediate to initiate a cascade reaction. The new method was applied to the first total synthesis of (±)-heliol.
报道了一种酸催化的非天然倍半萜双环[4 + 2]环加成反应。该关键环缩合反应通过生成活性邻醌甲醚中间体来引发级联反应，从而实现了从线性酚类前体到环状倍半萜的转化。该新方法被应用于（±）-heliol 的首次全合成。
