Altiti Ahmad S, Cheng Kai Fan, He Mingzhu, Al-Abed Yousef
Center for Molecular Innovation, The Feinstein Institute for Medical Research, 350 Community Drive, Manhasset, New York, 11030, USA.
Chemistry. 2017 Aug 10;23(45):10738-10743. doi: 10.1002/chem.201701944. Epub 2017 Jul 26.
A new synthetic protocol provides a simple and direct method to generate functionalized β-hydroxy-tetrahydroquinolines (THQs). Hydroboration of quinolines using chloroboranes followed by oxidation with NaBO ⋅H O led to the formation of functionalized β-hydroxy THQs. High regio- and diastereoselectivities were observed in α and γ substituted quinolines and the trans diastereomer of the β-hydroxy-THQ was the major isostere. This new protocol was utilized to build the novel antibody-targeted lupus peptidomimetic, FISLE-412.
一种新的合成方法提供了一种简单直接的方法来生成功能化的β-羟基-四氢喹啉（THQ）。使用氯硼烷对喹啉进行硼氢化反应，然后用NaBO·H₂O氧化，导致形成功能化的β-羟基THQ。在α和γ取代的喹啉中观察到了高区域选择性和非对映选择性，并且β-羟基-THQ的反式非对映异构体是主要的同分异构体。该新方法被用于构建新型抗体靶向的狼疮拟肽FISLE-412。
