A Palladium‐Catalyzed Aminoalkynylation Strategy towards Bicyclic Heterocycles: Synthesis of (±)‐Trachelanthamidine | Zendy

Nicolai Stefano | Zendy; Piemontesi Cyril | Zendy; Waser Jérôme | Zendy

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

Author(s) -

Nicolai Stefano,

Piemontesi Cyril,

Waser Jérôme

Publication year - 2011

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201100718

Subject(s) - palladium , bicyclic molecule , catalysis , chemistry , combinatorial chemistry , organic chemistry

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).

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