Jäger Sebastián N, Porta Exequiel O J, Labadie Guillermo R
Instituto de Química Rosario (IQUIR-CONICET), Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, S2002LRK, Rosario, Argentina.
Mol Divers. 2016 May;20(2):407-19. doi: 10.1007/s11030-015-9644-9. Epub 2015 Nov 3.
A diversity-oriented approach for the synthesis of various structurally different prenylated alcohols from readily accessible and common precursors was developed. With varying approaches, this article describes some successful examples of a Friedel-Crafts alkylation using methoxyphenols and different prenyl alcohols (geraniol and (E,E)-farnesol). We demonstrated that just by varying the stoichiometry of the Lewis acid used, the course of the reaction can be shifted to produce the alkylated or the cyclized product. Eighteen unique products were obtained with good isolated yields by direct alkylation with or without a consecutive π-cationic cyclization.
开发了一种以多样性为导向的方法，用于从易于获得的常见前体合成各种结构不同的异戊烯基化醇。通过不同的方法，本文描述了一些使用甲氧基苯酚和不同的异戊烯醇（香叶醇和（E,E）-法尼醇）进行傅克烷基化的成功实例。我们证明，仅仅通过改变所用路易斯酸的化学计量，反应过程就可以转向生成烷基化产物或环化产物。通过直接烷基化（有或没有连续的π-阳离子环化）以良好的分离产率获得了18种独特的产物。
