Document Detail


Tandem enyne metathesis-metallotropic [1,3]-shift for a concise total syntheses of (+)-asperpentyn, (-)-harveynone, and (-)-tricholomenyn A.
MedLine Citation:
PMID:  19115846     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
A tandem reaction sequence involving relay metathesis-induced enyne RCM and metallotropic [1,3]-shift is an effective tool to construct cyclic alkenes with embedded 1,5-dien-3-yne moieties from acyclic precursors containing a 1,3-diyne. Total syntheses of (+)-asperpentyn, (-)-harveynone, and (-)-tricholomenyn A have been accomplished by implementing this metathesis-based tandem reaction sequence as the key step.
Authors:
Jingwei Li; Sangho Park; Reagan L Miller; Daesung Lee
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural    
Journal Detail:
Title:  Organic letters     Volume:  11     ISSN:  1523-7052     ISO Abbreviation:  Org. Lett.     Publication Date:  2009 Feb 
Date Detail:
Created Date:  2009-01-29     Completed Date:  2009-02-26     Revised Date:  2013-06-02    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  United States    
Other Details:
Languages:  eng     Pagination:  571-4     Citation Subset:  IM    
Affiliation:
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607, USA.
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MeSH Terms
Descriptor/Qualifier:
Alkynes / chemical synthesis*,  chemistry
Biological Agents / chemical synthesis*,  chemistry
Catalysis
Cyclohexenes / chemical synthesis*,  chemistry
Epoxy Compounds / chemical synthesis*,  chemistry
Molecular Structure
Stereoisomerism
Grant Support
ID/Acronym/Agency:
CA106673/CA/NCI NIH HHS; R01 CA106673-04/CA/NCI NIH HHS
Chemical
Reg. No./Substance:
0/Alkynes; 0/Biological Agents; 0/Cyclohexenes; 0/Epoxy Compounds; 0/asperpentyn; 0/harveynone; 0/tricholomenyn A
Comments/Corrections

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