Synthesis of PPAR Agonist via Asymmetric Hydrogenation of a Cinnamic Acid Derivative and Stereospecific Displacement of (S)-2-Chloropropionic Acid

The synthesis of the peroxime proliferator activated receptor (PPAR) α,γ-agonist (1) was accomplished with high enantio- and diastereoselectivity by employing an asymmetric hydrogenation strategy, of an α-alkoxy cinnamic acid derivative, to set the C-2 chiral center. A diastereospecific SN2 displace...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2005-05, Vol.7 (10), p.1947-1950
Main Authors: Houpis, Ioannis N, Patterson, Lawrence E, Alt, Charles A, Rizzo, John R, Zhang, Tony Y, Haurez, Michael
Format: Article
Language:English
Subjects:
Cinnamates - chemistry
Combinatorial Chemistry Techniques
Hydrogenation
Molecular Structure
PPAR alpha - agonists
PPAR gamma - agonists
Propionates - chemical synthesis
Propionates - chemistry
Propionates - pharmacology
Stereoisomerism
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The synthesis of the peroxime proliferator activated receptor (PPAR) α,γ-agonist (1) was accomplished with high enantio- and diastereoselectivity by employing an asymmetric hydrogenation strategy, of an α-alkoxy cinnamic acid derivative, to set the C-2 chiral center. A diastereospecific SN2 displacement under mild basic conditions established the C-10 stereochemistry without any detectable racemization of the two epimerizable chiral centers.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol050367e