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    
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.
Nathan B Bennett; Allen Y Hong; Andrew M Harned; Brian M Stoltz
Related Documents :
22001739 - The reaction of h(2)s with oxidized thiols: generation of persulfides and implications ...
21861509 - Numerical construction of the $p_{fold}$ (committor) reaction coordinate for markov pro...
21824409 - Bkm-react, an integrated biochemical reaction database.
22057389 - Lack of correlation between catalytic efficiency and basicity of amines during the reac...
22038299 - A multi-component domino reaction for the direct access to polyfunctionalized indoles v...
21995549 - Copper-catalyzed iminoiodane-mediated aminolactonization of olefins: application to the...
24437719 - Finding the right (bioorthogonal) chemistry.
21581849 - (25r)-5a-spiro-stane-3,12-dione.
15283459 - Norisoprenoids and hepatoprotective flavone glycosides from the aerial parts of beta vu...
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    
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Heptanes / chemistry*
Grant Support
Reg. No./Substance:

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

Previous Document:  CT-Findings in Penetrating Captive Bolt Injuries to the Head and Brain: Analysis of the Trauma-Relat...
Next Document:  Effects of individual and social factors on preterm birth and low birth weight: empirical evidence f...