We thank the European Research Council (Advanced Grant No. 321066), the MINECO (CTQ2010-16088/BQU), and the ICIQ Foundation for financial support. We thank Elina Buitrago (visiting student from the University Stockholm) for experiments on the synthesis of (±)-3, and the ICIQ X-Ray Diffraction and Chromatograpy units.
Gold(I) as an Artificial Cyclase: Short Stereodivergent Syntheses of (−)-Epiglobulol and (−)-4β,7α- and (−)-4α,7α-Aromadendranediols†
Article first published online: 1 APR 2014
© 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 Non-Commercial License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
Angewandte Chemie International Edition
Volume 53, Issue 19, pages 4896–4899, May 5, 2014
How to Cite
Carreras, J., Livendahl, M., McGonigal, P. R. and Echavarren, A. M. (2014), Gold(I) as an Artificial Cyclase: Short Stereodivergent Syntheses of (−)-Epiglobulol and (−)-4β,7α- and (−)-4α,7α-Aromadendranediols. Angew. Chem. Int. Ed., 53: 4896–4899. doi: 10.1002/anie.201402044
- Issue published online: 2 MAY 2014
- Article first published online: 1 APR 2014
- Manuscript Received: 3 FEB 2014
- Funded Access
- European Research Council. Grant Number: 321066
- MINECO. Grant Number: CTQ2010-16088/BQU
- ICIQ Foundation
- natural products;
- total synthesis
Three natural aromadendrane sesquiterpenes, (−)-epiglobulol, (−)-4β,7α-aromadendranediol, and (−)-4α,7α-aromadendranediol, have been synthesized in only seven steps in 12, 15, and 17 % overall yields, respectively, from (E,E)-farnesol by a stereodivergent gold(I)-catalyzed cascade reaction which forms the tricyclic aromadendrane core in a single step. These are the shortest total syntheses of these natural compounds.