Biomimetic Total Synthesis of (±)-Garcibracteatone

The polycyclic polyprenylated acylphloroglucinol natural product garcibracteatone has been synthesized in four steps from phloroglucinol, using a strategy based on biosynthetic speculation. The key biomimetic transformation is a cascade of 7-endo-trig and 5-exo-trig radical cyclizations followed by...

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Bibliographic Details
Published in:Organic letters 2012-10, Vol.14 (19), p.5162-5164
Main Authors: Pepper, Henry P, Lam, Hiu C, Bloch, Witold M, George, Jonathan H
Format: Article
Language:English
Subjects:
Biomimetic Materials - chemical synthesis
Models, Molecular
Molecular Structure
Polycyclic Compounds - chemical synthesis
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Summary:The polycyclic polyprenylated acylphloroglucinol natural product garcibracteatone has been synthesized in four steps from phloroglucinol, using a strategy based on biosynthetic speculation. The key biomimetic transformation is a cascade of 7-endo-trig and 5-exo-trig radical cyclizations followed by a terminating aromatic substitution reaction.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol302524q