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Asymmetric Synthesis of the Major Metabolite of a Calcitonin Gene-Related Peptide Receptor Antagonist and Mechanism of Epoxide Hydrogenolysis
- Source :
- The Journal of Organic Chemistry. 82:3710-3720
- Publication Year :
- 2017
- Publisher :
- American Chemical Society (ACS), 2017.
-
Abstract
- An asymmetric synthesis of the major metabolite of the calcitonin gene-related peptide recepotor antagonist BMS-846372 is presented. The variously substituted cyclohepta[b]pyridine ring system represents an underexplored ring system and showed some unexpected chemistry. Reactivities of epoxide and ketone functional groups on the cycloheptane ring were extensively controlled by a remote bulky TIPS group. The rate difference of the hydrogenolysis between two diastereomeric epoxide intermediates shed some light on the mechanism of epoxide hydrogenolysis, and further, deuterium labeling studies revealed more mechanistic details on this well-known chemical transformation for the first time.
- Subjects :
- chemistry.chemical_classification
Ketone
010405 organic chemistry
Stereochemistry
Hydrolysis
Spectrum Analysis
Metabolite
Organic Chemistry
Enantioselective synthesis
Epoxide
Ring (chemistry)
Heterocyclic Compounds, 4 or More Rings
01 natural sciences
0104 chemical sciences
03 medical and health sciences
chemistry.chemical_compound
0302 clinical medicine
Calcitonin gene-related peptide receptor antagonist
chemistry
Calcitonin Gene-Related Peptide Receptor Antagonists
Hydrogenolysis
Epoxy Compounds
Cycloheptane
030217 neurology & neurosurgery
Subjects
Details
- ISSN :
- 15206904 and 00223263
- Volume :
- 82
- Database :
- OpenAIRE
- Journal :
- The Journal of Organic Chemistry
- Accession number :
- edsair.doi.dedup.....7a3498d965338d54a0b491ab7a51b05b