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?-Hydroxy-tetrahydroquinolines from Quinolines Using Chloroborane: Synthesis of the Peptidomimetic FISLE-412.

ABSTRACT: A new synthetic protocol provides a simple and direct method to generate functionalized ?-hydroxy-tetrahydroquinolines (THQs). Hydroboration of quinolines using chloroboranes followed by oxidation with NaBO3 ?H2 O led to the formation of functionalized ?-hydroxy THQs. High regio- and diastereoselectivities were observed in ? and ? substituted quinolines and the trans diastereomer of the ?-hydroxy-THQ was the major isostere. This new protocol was utilized to build the novel antibody-targeted lupus peptidomimetic, FISLE-412.

SUBMITTER: Altiti AS

PROVIDER: S-EPMC6003427 | biostudies-literature | 2017 Aug

REPOSITORIES: biostudies-literature

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β-Hydroxy-tetrahydroquinolines from Quinolines Using Chloroborane: Synthesis of the Peptidomimetic FISLE-412.

Altiti Ahmad S AS Cheng Kai Fan KF He Mingzhu M Al-Abed Yousef Y

Chemistry (Weinheim an der Bergstrasse, Germany) 20170726 45

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 ⋅H2 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 ...[more]

PMID: 28639294

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