We thank the Dulverton Trust for supporting this project and P. G. Turner, A. E. Gatland, and X. Yang for carrying out some preliminary experiments.
Interplay of Cascade Oxidative Cyclization and Hydride Shifts in the Synthesis of the ABC Spiroketal Ring System of Pectenotoxin-4†
Article first published online: 30 JAN 2013
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 52, Issue 9, pages 2491–2494, February 25, 2013
How to Cite
Donohoe, T. J. and Lipiński, R. M. (2013), Interplay of Cascade Oxidative Cyclization and Hydride Shifts in the Synthesis of the ABC Spiroketal Ring System of Pectenotoxin-4 . Angew. Chem. Int. Ed., 52: 2491–2494. doi: 10.1002/anie.201208919
- Issue published online: 19 FEB 2013
- Article first published online: 30 JAN 2013
- Manuscript Received: 7 NOV 2012
- natural products;
Concepts: The formation of stereochemically defined bis-THF units through a double cyclization and a hydride-shift-initiated route to spiroketals is described (see scheme; Xc=chiral auxiliary). The resulting sequence has been used in a synthesis of the C1–16 fragment of the naturally occurring antitumor agent pectenotoxin-4.