| Total syntheses of (-)-alpha-kainic acid and (+)-alpha-allokainic acid via stereoselective C-H insertion and efficient 3,4-stereocontrol. | |
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MedLine Citation:
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PMID: 18044924 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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. |
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Authors:
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Young Chun Jung; Cheol Hwan Yoon; Edward Turos; Kyung Soo Yoo; Kyung Woon Jung |
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Publication Detail:
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Type: Journal Article; Research Support, N.I.H., Extramural Date: 2007-11-29 |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 72 ISSN: 0022-3263 ISO Abbreviation: J. Org. Chem. Publication Date: 2007 Dec |
Date Detail:
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Created Date: 2007-12-14 Completed Date: 2008-03-25 Revised Date: 2013-06-06 |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 10114-22 Citation Subset: IM |
Affiliation:
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Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, California 90089-1062, USA. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Cyclization Kainic Acid / analogs & derivatives*, chemical synthesis*, chemistry Molecular Conformation Stereoisomerism |
| Grant Support | |
ID/Acronym/Agency:
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GM 71495/GM/NIGMS NIH HHS; R01 GM 62767/GM/NIGMS NIH HHS; R01 GM062767-05/GM/NIGMS NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/allokainic acid; 487-79-6/Kainic Acid |
| Comments/Corrections | |
Erratum In:
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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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