Asymmetric Synthesis of Heterocyclic Analogues of a CGRP Receptor Antagonist for Treating Migraine
| Autor: | Charles M. Conway, Gene M. Dubowchik, John E. Macor, Walter Kostich, Guanglin Luo, Ling Chen |
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| Rok vydání: | 2015 |
| Předmět: |
Molecular Structure
Pyrazine Pyridines Stereochemistry Migraine Disorders Aryl Organic Chemistry Enantioselective synthesis Diastereomer Stereoisomerism Biochemistry chemistry.chemical_compound Piperidines chemistry Calcitonin Gene-Related Peptide Receptor Antagonists Heck reaction Cycloheptanes Physical and Theoretical Chemistry Thiazole Cycloheptane |
| Zdroj: | Organic Letters. 17:5982-5985 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.5b02921 |
| Popis: | An asymmetric synthesis of novel heterocyclic analogue of the CGRP receptor antagonist rimegepant (BMS-927711, 3) is reported. The cycloheptane ring was constructed by an intramolecular Heck reaction. The application of Hayashi-Miyaura and Ellman reactions furnished the aryl and the amine chiral centers, while the separable diastereomeric third chiral center alcohols led to both carbamate and urea analogues. This synthetic approach was applicable to both 6- and 5-membered heterocycles as exemplified by pyrazine and thiazole derivatives. |
| Databáze: | OpenAIRE |
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