Stereoselective Synthesis of New Conformationally Restricted Analogues of a Potent CGRP Receptor Antagonist

A stereocontrolled racemic synthesis of conformationally restricted analogues 2a and 2b of a potent CGRP receptor antagonist 1 by novel functionalization of 2-substituted octahydropyrido[1,2-a]pyrazin-6-ones is described. The new diastereoselective LDA-promoted α-nitration of intermediate lactams es...

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Bibliographic Details
Published in:Organic letters 2005-06, Vol.7 (12), p.2465-2468
Main Authors: Zuev, Dmitry, Michne, Jodi A, Huang, Hong, Beno, Brett R, Wu, Dedong, Gao, Qi, Torrente, John R, Xu, Cen, Conway, Charles M, Macor, John E, Dubowchik, Gene M
Format: Article
Language:English
Subjects:
Benzimidazoles - chemical synthesis
Benzimidazoles - chemistry
Crystallography, X-Ray
Lactams - chemistry
Molecular Conformation
Molecular Structure
Piperazines - chemical synthesis
Piperazines - chemistry
Piperidines - chemical synthesis
Piperidines - chemistry
Pyrazines - chemistry
Receptors, Calcitonin Gene-Related Peptide - antagonists & inhibitors
Stereoisomerism
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Summary:A stereocontrolled racemic synthesis of conformationally restricted analogues 2a and 2b of a potent CGRP receptor antagonist 1 by novel functionalization of 2-substituted octahydropyrido[1,2-a]pyrazin-6-ones is described. The new diastereoselective LDA-promoted α-nitration of intermediate lactams established the required trans-configuration in the desired products.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0510062