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
Hauptverfasser: Duspara, Petar A., Batey, Robert A.
Format: Artikel
Sprache:eng
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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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201304759