School of Chemistry and Materials Science, Jiangsu Normal University , Xuzhou 221116, Jiangsu, China.
Org Lett. 2018 Feb 16;20(4):1122-1125. doi: 10.1021/acs.orglett.8b00045. Epub 2018 Feb 5.
The development of a rapid, highly efficient, and one-pot synthesis of C3-α-prenylated oxindoles with simple reagents is described. The process is based on zinc-mediated α-regioselective prenylation of 3-acylidene-oxindole with commercially available prenyl bromide using inexpensive CeCl as the catalyst. The new transformation tolerates a wide range of 3-acylidene-oxindoles, providing easy access to a variety of functionalized 3-prenylated oxindoles. The synthetic utility of the approach is verified by formal synthesis of the flustramine family alkaloid (±)-debromoflustramine E.
本文描述了一种快速、高效、一锅法合成 C3-α-位prenylated 氧吲哚的方法，所用试剂简单。该过程基于锌介导的 3-酰亚烯基氧吲哚与商业上可获得的prenyl 溴的α-区域选择性prenylation，使用廉价的 CeCl 作为催化剂。新的转化可以容忍广泛的 3-酰亚烯基氧吲哚，为各种功能化的 3-位prenylated 氧吲哚的合成提供了便利。该方法的合成实用性通过 flustramine 家族生物碱（±）-debromoflustramine E 的形式合成得到了验证。
