The EPFL and the SNF (grant number 200021_119810) are acknowledged for financial support.
A Palladium-Catalyzed Aminoalkynylation Strategy towards Bicyclic Heterocycles: Synthesis of (±)-Trachelanthamidine†
Article first published online: 15 APR 2011
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 50, Issue 20, pages 4680–4683, May 9, 2011
How to Cite
Nicolai, S., Piemontesi, C. and Waser, J. (2011), A Palladium-Catalyzed Aminoalkynylation Strategy towards Bicyclic Heterocycles: Synthesis of (±)-Trachelanthamidine. Angew. Chem. Int. Ed., 50: 4680–4683. doi: 10.1002/anie.201100718
- Issue published online: 4 MAY 2011
- Article first published online: 15 APR 2011
- Manuscript Received: 28 JAN 2011
- heterocyclic compounds;
- hypervalent iodine
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).