A Short Total Synthesis of the Marine Sponge Pyrrole-2-aminoimidazole Alkaloid (±)-Agelastatin A
Ring by ring: (±)‐Agelastatin A has been synthesized through the use of domino and one‐pot reactions while minimizing protecting group usage. The core was accessed through a stereoselective domino condensation/ring‐opening/4π‐conrotatory electrocyclization and elaborated using newly developed protoc...
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Veröffentlicht in: | Angewandte Chemie International Edition 2013-10, Vol.52 (41), p.10862-10866 |
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Hauptverfasser: | , |
Format: | Artikel |
Sprache: | eng |
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Online-Zugang: | Volltext |
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Zusammenfassung: | Ring by ring: (±)‐Agelastatin A has been synthesized through the use of domino and one‐pot reactions while minimizing protecting group usage. The core was accessed through a stereoselective domino condensation/ring‐opening/4π‐conrotatory electrocyclization and elaborated using newly developed protocols for urea and amide formation. Oxidation of an unprotected pre‐agelastatin A and an intramolecular aza‐Michael reaction completed the synthesis in only six steps. |
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ISSN: | 1433-7851 1521-3773 |
DOI: | 10.1002/anie.201304759 |