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Asymmetric Synthesis of Fluoro‐MLN4924 as a Selective NEDD8‐Activating Enzyme (NAE) Inhibitor
Author(s) -
Kim HongRae,
Jarhad Dnyandev B.,
Sahu Pramod K.,
Sung Kisu,
An Dayoung,
Hyun Young Eum,
Yu Jinha,
Jeong Lak Shin
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900350
Subject(s) - chemistry , regioselectivity , stereoselectivity , stereochemistry , enzyme , cleavage (geology) , combinatorial chemistry , organic chemistry , catalysis , geotechnical engineering , fracture (geology) , engineering
Based on bioisosteric rationale, fluorinated analogues of MLN4924, which is a selective NEDD8‐activating enzyme inhibitor, were designed and their asymmetric syntheses were accomplished via stereoselective reduction, regioselective isopropylidene cleavage and diethylaminosulfur trifluoride (DAST) fluorination as key steps.