Document Detail


Synthesis of enantioenriched γ-quaternary cycloheptenones using a combined allylic alkylation/Stork-Danheiser approach: preparation of mono-, bi-, and tricyclic systems.
MedLine Citation:
PMID:  22009489     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
A general method for the synthesis of β-substituted and unsubstituted cycloheptenones bearing enantioenriched all-carbon γ-quaternary stereocenters is reported. Hydride or organometallic addition to a seven-membered ring vinylogous ester followed by finely tuned quenching parameters achieves elimination to the corresponding cycloheptenone. The resulting enones are elaborated to bi- and tricyclic compounds with potential for the preparation of non-natural analogs and whose structures are embedded in a number of cycloheptanoid natural products.
Authors:
Nathan B Bennett; Allen Y Hong; Andrew M Harned; 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:  2011-10-19
Journal Detail:
Title:  Organic & biomolecular chemistry     Volume:  10     ISSN:  1477-0539     ISO Abbreviation:  Org. Biomol. Chem.     Publication Date:  2012 Jan 
Date Detail:
Created Date:  2011-12-05     Completed Date:  2012-03-19     Revised Date:  2014-09-17    
Medline Journal Info:
Nlm Unique ID:  101154995     Medline TA:  Org Biomol Chem     Country:  England    
Other Details:
Languages:  eng     Pagination:  56-9     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
Alkylation
Heptanes / chemistry*
Stereoisomerism
Grant Support
ID/Acronym/Agency:
R01 GM080269/GM/NIGMS NIH HHS; R01GM080269-01/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
0/Heptanes
Comments/Corrections

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