Biomimetic Total Synthesis of Meiogynin A, an Inhibitor of Bcl-xL and Bak Interaction

A short, convergent, and selective synthesis of meiogynin A, an inhibitor of the antiapoptotic protein Bcl-xL, has been performed. This synthesis, based on a biomimetic approach, allowed the determination of its absolute configuration. Three isomers of meiogynin A have also been elaborated. One of t...

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Bibliographic Details
Published in:Journal of organic chemistry 2010-11, Vol.75 (21), p.7412-7415
Main Authors: Fotsop, Dalia Fomekong, Roussi, Fanny, Leverrier, Aurélie, Bretéché, Anne, Guéritte, Françoise
Format: Article
Language:English
Subjects:
bcl-2 Homologous Antagonist-Killer Protein - metabolism
bcl-X Protein - metabolism
Biomimetics
Chemical Sciences
Chemistry
Condensed benzenic and aromatic compounds
Exact sciences and technology
Isomerism
Organic chemistry
Preparations and properties
Protein Binding - drug effects
Sesquiterpenes - chemical synthesis
Sesquiterpenes - chemistry
Sesquiterpenes - pharmacology
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Summary:A short, convergent, and selective synthesis of meiogynin A, an inhibitor of the antiapoptotic protein Bcl-xL, has been performed. This synthesis, based on a biomimetic approach, allowed the determination of its absolute configuration. Three isomers of meiogynin A have also been elaborated. One of these was found to be three times more potent than the natural compound.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo101088h