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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).