Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster , Corrensstr. 40, 48149 Münster, Germany.
Org Lett. 2018 Feb 2;20(3):724-727. doi: 10.1021/acs.orglett.7b03859. Epub 2018 Jan 16.
Routes to prepare C4-trifluoromethyl analogues of the 2H-chromene scaffold are scarce: this is particularly striking given the importance of fluorine in pharmaceutical development. To address this limitation, a facile strategy has been developed that is reliant on catalytic, geometric isomerization of easily accessible allylic alcohols (up to >95:5) followed by intramolecular cyclization via Pd catalysis (up to 96%). This concise biomimetic approach emulates the photoisomerization/cyclization cascade inherent to phenylpropanoid biosynthesis.
制备 2H-色烯支架的 C4-三氟甲基类似物的途径很少：考虑到氟在药物开发中的重要性，这一点尤其引人注目。为了解决这一限制，开发了一种简便的策略，该策略依赖于容易获得的烯丙醇的催化、几何异构化（高达>95:5），然后通过 Pd 催化进行分子内环化（高达 96%）。这种简洁的仿生方法模拟了苯丙氨酸生物合成中固有的光异构化/环化级联。
