Document Detail


Enantioselective synthesis of a hydroxymethyl-cis-1,3-cyclopentenediol building block.
MedLine Citation:
PMID:  23101616     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
A brief, enantioselective synthesis of a hydroxymethyl-cis-1,3-cyclopentenediol building block is presented. This scaffold allows access to the cis-1,3-cyclopentanediol fragments found in a variety of biologically active natural and non-natural products. This rapid and efficient synthesis is highlighted by the utilization of the palladium-catalyzed enantioselective allylic alkylation of dioxanone substrates to prepare tertiary alcohols.
Authors:
Robert A Craig; Jennifer L Roizen; Russell C Smith; Amanda C Jones; Brian M Stoltz
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't     Date:  2012-10-26
Journal Detail:
Title:  Organic letters     Volume:  14     ISSN:  1523-7052     ISO Abbreviation:  Org. Lett.     Publication Date:  2012 Nov 
Date Detail:
Created Date:  2012-11-16     Completed Date:  2013-04-11     Revised Date:  2013-12-04    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  United States    
Other Details:
Languages:  eng     Pagination:  5716-9     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
Alcohols / chemical synthesis*,  chemistry
Alkylation
Catalysis
Cyclopentanes / chemical synthesis*,  chemistry
Dioxanes / chemistry*
Molecular Structure
Palladium / chemistry*
Stereoisomerism
Grant Support
ID/Acronym/Agency:
F32GM082000/GM/NIGMS NIH HHS; R01 GM080269/GM/NIGMS NIH HHS; R01GM080269-01/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
0/Alcohols; 0/Cyclopentanes; 0/Dioxanes; 5TWQ1V240M/Palladium
Comments/Corrections

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