title: Stereoselective synthesis of MLN4924, an inhibitor of NEDD8-activating enzyme.
abstract: MLN4924 (1), which is in clinical trials as an anticancer agent, was stereoselectively synthesized from d-ribose via a route involving stereoselective reduction, regioselective cleavage of an isopropylidene moiety, and selective displacement of a cyclic sulfate moiety as key steps.
authors.affiliation: Department of Bioinspired Science and Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120-750, Korea.
authors.forename: Hyuk Woo
authors.initials: HW
authors.lastname: Lee
authors.forename: Soo Kyung
authors.initials: SK
authors.lastname: Nam
authors.forename: Won Jun
authors.initials: WJ
authors.lastname: Choi
authors.forename: Hea Ok
authors.initials: HO
authors.lastname: Kim
authors.forename: Lak Shin
authors.initials: LS
authors.lastname: Jeong
mesh_terms: D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism; D013379:Substrate Specificity; D014452:Ubiquitins / Q000037:antagonists & inhibitors* / Q000378:metabolism
chemical_list: D003517:Cyclopentanes; D011743:Pyrimidines; D014452:Ubiquitins; C539933:pevonedistat