title: Efficient and scalable enantioselective synthesis of a CGRP antagonist.
abstract: An enantioselective synthesis of the CGRP antagonist BMS-846372, amenable to large scale preparation, is presented. This new synthesis showcases a chemo- and enantioselective reduction of a cyclohepta[b]pyridine-5,9-dione as well as a Pd-catalyzed alpha-arylation reaction to form the key carbon-carbon bond and set the absolute and relative stereochemistry.
authors.affiliation: Chemical Development and Drug Product Science and Technology, Bristol-Myers Squibb Company, One Squibb Drive, New Brunswick, New Jersey 08903, USA. david.leahy@bms.com
authors.forename: David K
authors.initials: DK
authors.lastname: Leahy
authors.forename: Yu
authors.initials: Y
authors.lastname: Fan
authors.forename: Lopa V
authors.initials: LV
authors.lastname: Desai
authors.forename: Collin
authors.initials: C
authors.lastname: Chan
authors.forename: Jason
authors.initials: J
authors.lastname: Zhu
authors.forename: Guanglin
authors.initials: G
authors.lastname: Luo
authors.forename: Ling
authors.initials: L
authors.lastname: Chen
authors.forename: Ronald L
authors.initials: RL
authors.lastname: Hanson
authors.forename: Masano
authors.initials: M
authors.lastname: Sugiyama
authors.forename: Thorsten
authors.initials: T
authors.lastname: Rosner
authors.forename: Nicolas
authors.initials: N
authors.lastname: Cuniere
authors.forename: Zhiwei
authors.initials: Z
authors.lastname: Guo
authors.forename: Yi
authors.initials: Y
authors.lastname: Hsiao
authors.forename: Qi
authors.initials: Q
authors.lastname: Gao
mesh_terms: D015740:Calcitonin Gene-Related Peptide / Q000037:antagonists & inhibitors*; D002384:Catalysis; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: C576963:BMS-846372; D006576:Heterocyclic Compounds, 4 or More Rings; D015740:Calcitonin Gene-Related Peptide