Synthesis of the Tetracyclic Core of Exiguaquinol

Synthesis of the Tetracyclic Core of Exiguaquinol

A Diels–Alder reaction, a desymmetrizing aldol reaction, and a reductive Heck cyclization are employed in a short synthesis of a tetracycle relevant to exiguaquinol, a potential antibiotic. Ground-state energies of this advanced model system and the natural product rationalize the incorrect hemiamin...

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Veröffentlicht in:Organic letters 2013-12, Vol.15 (23), p.6014-6017
Hauptverfasser: Schwarzwalder, Gregg M, Steinhardt, Sarah E, Pham, Hung V, Houk, K. N, Vanderwal, Christopher D
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes
Crystallography, X-Ray
Cyclization
Cycloaddition Reaction
Helicobacter pylori - drug effects
Helicobacter pylori - enzymology
Hydroquinones - chemical synthesis
Hydroquinones - chemistry
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Stereoisomerism
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Beschreibung
Zusammenfassung:A Diels–Alder reaction, a desymmetrizing aldol reaction, and a reductive Heck cyclization are employed in a short synthesis of a tetracycle relevant to exiguaquinol, a potential antibiotic. Ground-state energies of this advanced model system and the natural product rationalize the incorrect hemiaminal configuration experimentally obtained and point to the importance of the sulfonate in dictating the relative configuration of the natural product.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol402905n