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- Title
β-Hydroxy-tetrahydroquinolines from Quinolines Using Chloroborane: Synthesis of the Peptidomimetic FISLE-412.
- Authors
Altiti, Ahmad S.; Cheng, Kai Fan; He, Mingzhu; Al‐Abed, Yousef
- Abstract
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 NaBO3⋅H2O 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.
- Subjects
HYDROXY acids; QUINOLINE; PEPTIDOMIMETICS; REGIOSELECTIVITY (Chemistry); DIASTEREOISOMERS
- Publication
Chemistry - A European Journal, 2017, Vol 23, Issue 45, p10738
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201701944