Document Detail


Divergent syntheses of resorcylic acid lactones: L-783277, LL-Z1640-2, and hypothemycin.
MedLine Citation:
PMID:  19821460     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The resorcylic acid lactones (RAL) are endowed with diverse biological activity ranging from transcription factor modulators (zearalenone and zearalenol) to HSP90 inhibitors (radicicol and pochonin D) and reversible (aigialomycin D) as well as irreversible kinase inhibitors (hypothemycin and other RAL containing a cis-enone). Our interest in broadening the diversity of this family beyond naturally occurring diversity has led us to seek a general approach that could be used to address the entire spectrum of functionalities present within this family. Herein, we present our efforts on accessing macrocycles bearing an alkane, alkene, or epoxide at the benzylic position from a common benzylic sulfide intermediate to access L-783277, LL-Z1640-2, and hypothemycin.
Authors:
Pierre-Yves Dakas; Rajamalleswaramma Jogireddy; Ga??lle Valot; Sofia Barluenga; Nicolas Winssinger
Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Chemistry (Weinheim an der Bergstrasse, Germany)     Volume:  15     ISSN:  1521-3765     ISO Abbreviation:  Chemistry     Publication Date:  2009 Nov 
Date Detail:
Created Date:  2009-10-29     Completed Date:  2010-01-15     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9513783     Medline TA:  Chemistry     Country:  Germany    
Other Details:
Languages:  eng     Pagination:  11490-7     Citation Subset:  IM    
Affiliation:
Institut de Science et Ing??nierie Supramol??culaires (ISIS-UMR 7006), Universit?? de Strasbourg-CNRS, 8 all??e Gaspard Monge, 67000 Strasbourg, France.
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MeSH Terms
Descriptor/Qualifier:
Alkylation
HSP90 Heat-Shock Proteins / antagonists & inhibitors,  metabolism
Hydroxybenzoic Acids / chemistry*
Lactones / chemical synthesis*,  chemistry
Oxidation-Reduction
Protein Kinase Inhibitors / chemical synthesis*,  chemistry
Resorcinols / chemical synthesis*,  chemistry
Safrole / analogs & derivatives,  chemistry
Stereoisomerism
Sulfides / chemistry
Zearalenone / analogs & derivatives,  chemical synthesis,  chemistry
Chemical
Reg. No./Substance:
0/HSP90 Heat-Shock Proteins; 0/Hydroxybenzoic Acids; 0/L 783277; 0/LL Z1640-2; 0/Lactones; 0/Protein Kinase Inhibitors; 0/Resorcinols; 0/Sulfides; 0/hypothemycin; 120-62-7/sulfoxide; 17924-92-4/Zearalenone; 94-59-7/Safrole

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


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