Document Detail


Syntheses of papyracillic acids: application of the tandem chain extension-acylation reaction.
MedLine Citation:
PMID:  23013246     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
A synthetic approach to the papyracillic acid family of natural products has been developed. The spiroacetal core is rapidly assembled through an unprecedented zinc carbenoid-mediated tandem chain extension-acylation reaction. Subsequent functional group manipulation provided access to papyracillic acid B and 4-epi-papyracillic acid C. The successful preparation of these molecules resulted in the clarification of structural assignments of members of this family of natural products.
Authors:
Jennifer R Mazzone; Charles K Zercher
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural     Date:  2012-10-05
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  77     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2012 Oct 
Date Detail:
Created Date:  2012-10-19     Completed Date:  2013-03-22     Revised Date:  2013-10-22    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  9171-8     Citation Subset:  IM    
Affiliation:
Department of Chemistry, University of New Hampshire, Durham, New Hampshire 03824, USA.
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MeSH Terms
Descriptor/Qualifier:
Acylation
Alkenes / chemical synthesis*,  chemistry
Molecular Structure
Spiro Compounds / chemical synthesis*,  chemistry
Grant Support
ID/Acronym/Agency:
R15 GM060967/GM/NIGMS NIH HHS; R15 GM060967-02/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
0/Alkenes; 0/Spiro Compounds; 0/papyracillic acid
Comments/Corrections

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