Document Detail


Total syntheses of (-)-alpha-kainic acid and (+)-alpha-allokainic acid via stereoselective C-H insertion and efficient 3,4-stereocontrol.
MedLine Citation:
PMID:  18044924     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Reported herein is a novel approach to the total syntheses of (-)-alpha-kainic acid and (+)-alpha-allokainic acid, where the stereochemistries on C(2), C(3), and C(4) of the pyrrolidine core were introduced efficiently and selectively. A regio- and stereoselective C-H insertion reaction was utilized to prepare the gamma-lactam as an intermediate. A Michael-type cyclization of phenylsulfone with a conjugated acetylenic ketone was developed to prepare the tricyclic ketone as a key intermediate for (-)-alpha-kainic acid. Subsequently, a stereoselective dephenylsulfonylation was carried out successfully to secure the cis relationship at C(3) and C(4) centers. An unprecedented acetylation on the phenylsulfone, followed by a stereoselective dephenylsulfonylation, secured the trans relationship at C(3) and C(4) centers in (+)-alpha-allokainic acid.
Authors:
Young Chun Jung; Cheol Hwan Yoon; Edward Turos; Kyung Soo Yoo; Kyung Woon Jung
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural     Date:  2007-11-29
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  72     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2007 Dec 
Date Detail:
Created Date:  2007-12-14     Completed Date:  2008-03-25     Revised Date:  2013-06-06    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  10114-22     Citation Subset:  IM    
Affiliation:
Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, California 90089-1062, USA.
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MeSH Terms
Descriptor/Qualifier:
Cyclization
Kainic Acid / analogs & derivatives*,  chemical synthesis*,  chemistry
Molecular Conformation
Stereoisomerism
Grant Support
ID/Acronym/Agency:
GM 71495/GM/NIGMS NIH HHS; R01 GM 62767/GM/NIGMS NIH HHS; R01 GM062767-05/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
0/allokainic acid; 487-79-6/Kainic Acid
Comments/Corrections
Erratum In:
J Org Chem. 2008 Apr 4;73(7):2959

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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