Document Detail


Free-radical-mediated conjugate additions. Enantioselective synthesis of butyrolactone natural products: (-)-enterolactone, (-)-arctigenin, (-)-isoarctigenin, (-)-nephrosteranic acid, and (-)-roccellaric acid.
MedLine Citation:
PMID:  11895386     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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.
Authors:
Mukund P Sibi; Pingrong Liu; Jianguo Ji; Saumen Hajra; Jian-xie Chen
Related Documents :
12645016 - Multisite catalysis: a mechanistic study of beta-lactone synthesis from epoxides and co...
9737006 - The effect of organic solvents on the determination of cyclic boronates of some beta-bl...
20919686 - Evaluation of catalyst acidity and substrate electronic effects in a hydrogen bond-cata...
22109846 - Experimental sink removal induces stress responses, including shifts in amino acid and ...
9552716 - Inhibition of listeria monocytogenes and salmonella enteriditis by combinations of plan...
1801316 - Isolation of neurotoxic peptides from the venom of the 'armed' spider phoneutria nigriv...
Publication Detail:
Type:  Journal Article; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  67     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2002 Mar 
Date Detail:
Created Date:  2002-03-15     Completed Date:  2002-06-17     Revised Date:  2007-11-14    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  1738-45     Citation Subset:  IM    
Affiliation:
Department of Chemistry, North Dakota State University, Fargo, North Dakota 58105-5516, USA. Mukund.Sibi@ndsu.nodak.edu
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Descriptor/Qualifier:
4-Butyrolactone / 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:
GM-54656/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
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


Previous Document:  The preorganization step in organic reaction mechanisms. Charge-transfer complexes as precursors to ...
Next Document:  Directing abilities of alcohol-derived functional groups in the hydroformylation of olefins.