Total Synthesis and Stereochemistry of Uncialamycin

Total Synthesis and Stereochemistry of Uncialamycin

Unseal the secrets of uncialamycin: The total synthesis of the C26 epimers of the newly discovered enediyne natural product allows its stereochemical assignment and further biological investigations of this potent antibiotic. Key steps involve the addition of an acetylide to a pyridinium species, an...

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Veröffentlicht in:Angewandte Chemie International Edition 2007-01, Vol.46 (25), p.4704-4707
Hauptverfasser: Nicolaou, K. C., Zhang, Hongjun, Chen, Jason S., Crawford, James J., Pasunoori, Laxman
Format: Artikel
Sprache:eng
Schlagworte:
Anthraquinones - chemical synthesis
Anthraquinones - chemistry
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - chemistry
antibiotics
enediynes
Models, Molecular
Molecular Conformation
Molecular Structure
natural products
Stereoisomerism
Streptomyces - chemistry
structure elucidation
total synthesis
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Beschreibung
Zusammenfassung:Unseal the secrets of uncialamycin: The total synthesis of the C26 epimers of the newly discovered enediyne natural product allows its stereochemical assignment and further biological investigations of this potent antibiotic. Key steps involve the addition of an acetylide to a pyridinium species, an intramolecular formation of the enediyne, and Hauser annulation to form the anthraquinone moiety.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200700917