Gold-Catalyzed One-Step Construction of 2,3-Dihydro-1H-Pyrrolizines with an Electron-Withdrawing group in the 5-position: A Formal Synthesis of 7-Methoxymitosene

What a ring formation! Bicyclic dihydropyrrolizines with an electron‐withdrawing group (EWG) at the 5‐position are formed in one step from linear azidoenynes under gold catalysis. This novel route involves the use of azide as a nitrene precursor, electronically‐controlled regioselectivity, and the g...

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Veröffentlicht in:	Angewandte Chemie International Edition 2012-08, Vol.51 (34), p.8624-8627
Hauptverfasser:	Yan, Ze-Yi, Xiao, Yuanjing, Zhang, Liming
Format:	Artikel
Sprache:	eng
Schlagworte:	Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - chemistry carbene Catalysis Chemistry, Pharmaceutical Construction Formations Gold Gold - chemistry homogeneous catalysis Mitomycins - chemical synthesis Mitomycins - chemistry mitosene Molecular Structure nitrene Precursors Pyrroles - chemical synthesis Pyrroles - chemistry Regioselectivity Stereoisomerism Synthesis
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Beschreibung
Zusammenfassung:	What a ring formation! Bicyclic dihydropyrrolizines with an electron‐withdrawing group (EWG) at the 5‐position are formed in one step from linear azidoenynes under gold catalysis. This novel route involves the use of azide as a nitrene precursor, electronically‐controlled regioselectivity, and the generation of destabilized 1‐azapentadienium ions and their pericyclic reactions. This method was used for a formal synthesis of 7‐methoxymitosene (see scheme).
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.201203678