Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul 08826, Korea.
J Org Chem. 2021 Jul 16;86(14):9828-9837. doi: 10.1021/acs.joc.1c00705. Epub 2021 Jun 29.
To determine which sugar conformation is favorable in binding to peroxisome proliferator-activated receptors, the conformationally locked south () and north () analogues were asymmetrically synthesized using a bicyclo[3.1.0]hexane template. The ()-conformer was synthesized by employing "reagent-controlled" Charette asymmetric cyclopropanation in a 100% stereoselective manner, whereas the ()-conformer was stereoselectively synthesized by using "substrate-controlled" hydroxyl-directed Simmons-Smith cyclopropanation as a key step.
为了确定哪种糖构象有利于与过氧化物酶体增殖物激活受体结合，使用双环[3.1.0]己烷模板不对称合成了构象锁定的南（）和北（）类似物。通过采用“试剂控制”的 Charette 不对称环丙烷化反应以 100%立体选择性的方式合成了（）-构象体，而（）-构象体则通过使用“底物控制”的羟基导向 Simmons-Smith 环丙烷化作为关键步骤立体选择性地合成。
