A Palladium-Catalyzed Aminoalkynylation Strategy towards Bicyclic Heterocycles: Synthesis of (±)-Trachelanthamidine

A Palladium-Catalyzed Aminoalkynylation Strategy towards Bicyclic Heterocycles: Synthesis of (±)-Trachelanthamidine

Sweet cyclizations: The synthesis of pyrrolizidines and indolizidines has been achieved. Olefins were subjected to an intramolecular palladium‐catalyzed aminoalkynylation with the hypervalent iodine reagent TIPS‐EBX. After removal of the protecting group, a two‐step cyclization sequence and subseque...

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Veröffentlicht in:Angewandte Chemie International Edition 2011-05, Vol.50 (20), p.4680-4683
Hauptverfasser: Nicolai, Stefano, Piemontesi, Cyril, Waser, Jérôme
Format: Artikel
Sprache:eng
Schlagworte:
alkaloids
Alkynes - chemistry
alkynylation
Amides - chemistry
amination
Bridged Bicyclo Compounds, Heterocyclic - chemical synthesis
Bridged Bicyclo Compounds, Heterocyclic - chemistry
Catalysis
heterocyclic compounds
hypervalent iodine
Molecular Structure
Organometallic Compounds - chemistry
Palladium
Palladium - chemistry
Pyrrolizidine Alkaloids - chemical synthesis
Pyrrolizidine Alkaloids - chemistry
Stereoisomerism
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Zusammenfassung:Sweet cyclizations: The synthesis of pyrrolizidines and indolizidines has been achieved. Olefins were subjected to an intramolecular palladium‐catalyzed aminoalkynylation with the hypervalent iodine reagent TIPS‐EBX. After removal of the protecting group, a two‐step cyclization sequence and subsequent reduction led to the natural product (±)‐trachelanthamidine (see scheme; TIPS‐EBX=triisopropylsilyl ethynylbenziodoxolone).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201100718