| Free-radical-mediated conjugate additions. Enantioselective synthesis of butyrolactone natural products: (-)-enterolactone, (-)-arctigenin, (-)-isoarctigenin, (-)-nephrosteranic acid, and (-)-roccellaric acid. | |
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MedLine Citation:
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PMID: 11895386 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Lewis acid-mediated conjugate addition of alkyl radicals to a differentially protected fumarate 10 produced the monoalkylated succinates with high chemical efficiency and excellent stereoselectivity. A subsequent alkylation or an aldol reaction furnished the disubstituted succinates with syn configuration. The chiral auxiliary, 4-diphenylmethyl-2-oxazolidinone, controlled the stereoselectivity in both steps. Manipulation of the disubstituted succinates obtained by alkylation furnished the natural products (-)-enterolactone, (-)-arctigenin, and (-)-isoarctigenin. The overall yields for the target natural products were 20-26% over six steps. Selective functionalization of the disubstituted succinates obtained by aldol condensation gave the paraconic acid natural products (-)-nephrosteranic acid (8) and (-)-roccellaric acid (9). The overall yield of the natural products 8 and 9 over four steps was 53% and 42%, respectively. |
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Authors:
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Mukund P Sibi; Pingrong Liu; Jianguo Ji; Saumen Hajra; Jian-xie Chen |
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Publication Detail:
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Type: Journal Article; Research Support, U.S. Gov't, P.H.S. |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 67 ISSN: 0022-3263 ISO Abbreviation: J. Org. Chem. Publication Date: 2002 Mar |
Date Detail:
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Created Date: 2002-03-15 Completed Date: 2002-06-17 Revised Date: 2007-11-14 |
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: 1738-45 Citation Subset: IM |
Affiliation:
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Department of Chemistry, North Dakota State University, Fargo, North Dakota 58105-5516, USA. Mukund.Sibi@ndsu.nodak.edu |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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4-Butyrolactone
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analogs & derivatives*,
chemical synthesis,
chemistry Alkylation Biological Products / chemical synthesis*, chemistry* Catalysis Chemistry, Organic / methods Free Radicals / chemistry* Fumarates / chemistry Furans / chemical synthesis, chemistry Lactones / chemistry Lignans / chemical synthesis, chemistry Magnetic Resonance Spectroscopy Molecular Structure Stereoisomerism Succinates / chemistry |
| Grant Support | |
ID/Acronym/Agency:
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GM-54656/GM/NIGMS NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Biological Products; 0/Free Radicals; 0/Fumarates; 0/Furans; 0/Lactones; 0/Lignans; 0/Succinates; 0/isoarctigenin; 0/nephrosteranic acid; 0/roccellaric acid; 76543-15-2/2,3-bis(3'-hydroxybenzyl)butyrolactone; 7770-78-7/arctigenin; 96-48-0/4-Butyrolactone |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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