Synthetic Studies Towards the Core Structure of Nakadomarin A by a Thioamide-Based Strategy
Article first published online: 14 NOV 2013
© 2014 The Authors. Published by WILEY-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
European Journal of Organic Chemistry
Volume 2014, Issue 1, pages 129–139, January 2014
How to Cite
Chavda, J. K., Procopiou, P. A., Horton, P. N., Coles, S. J. and Porter, M. J. (2014), Synthetic Studies Towards the Core Structure of Nakadomarin A by a Thioamide-Based Strategy. Eur. J. Org. Chem., 2014: 129–139. doi: 10.1002/ejoc.201301063
- Issue published online: 18 DEC 2013
- Article first published online: 14 NOV 2013
- Manuscript Received: 17 JUL 2013
- Funded Access
- Natural products;
- Sigmatropic rearrangement;
- Multicomponent reactions
The tricyclic BCD substructure of the marine natural product nakadomarin A has been synthesised. The strategy utilised a key carbon–carbon bond-forming reaction between a furan and an N-acyliminium ion derived from a secondary thiolactam. In addition, a novel three-component coupling reaction between a thioamide, an allylic bromide and an isocyanate, leading to the establishment of two new stereogenic centres, is reported.