Document Detail

Generation and hetero-Diels-Alder reactions of an o-quinone methide under mild, anionic conditions: rapid synthesis of mono-benzannelated spiroketals.
MedLine Citation:
PMID:  18633540     Owner:  NLM     Status:  MEDLINE    
Deprotonation of o-hydroxybenzyl acetate with (i)PrMgCl provides a method of generating an o-quinone methide under mild, anionic conditions, such that highly sensitive exo-enol ethers can be employed as 2pi partners in hetero-Diels-Alder reactions. This process results in mono-benzannelated spiroketals such as those found in the natural products berkelic acid, the chaetoquadrins or cephalostatin 6.
Christopher D Bray
Publication Detail:
Type:  Journal Article     Date:  2008-05-28
Journal Detail:
Title:  Organic & biomolecular chemistry     Volume:  6     ISSN:  1477-0520     ISO Abbreviation:  Org. Biomol. Chem.     Publication Date:  2008 Aug 
Date Detail:
Created Date:  2008-07-17     Completed Date:  2008-10-14     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101154995     Medline TA:  Org Biomol Chem     Country:  England    
Other Details:
Languages:  eng     Pagination:  2815-9     Citation Subset:  IM    
School of Biological and Chemical Sciences, The Walter Besant Building, Queen Mary, University of London, London, UK.
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MeSH Terms
Anions / chemistry
Benzene Derivatives / chemical synthesis,  chemistry*
Furans / chemical synthesis*
Indolequinones / chemical synthesis,  chemistry*
Molecular Structure
Spiro Compounds / chemical synthesis*
Reg. No./Substance:
0/Anions; 0/Benzene Derivatives; 0/Furans; 0/Indolequinones; 0/Protons; 0/Spiro Compounds; 0/spiroketal; 138230-21-4/quinone methide

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

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