Gold(I) as an Artificial Cyclase: Short Stereodivergent Syntheses of (−)-Epiglobulol and (−)-4β,7α- and (−)-4α,7α-Aromadendranediols

Carreras, Javier; Livendahl, Madeleine; McGonigal, Paul R.; Echavarren, Antonio M.

doi:10.1002/anie.201402044

Gold(I) as an Artificial Cyclase: Short Stereodivergent Syntheses of (−)-Epiglobulol and (−)-4β,7α- and (−)-4α,7α-Aromadendranediols

Carreras, Javier; Livendahl, Madeleine; McGonigal, Paul R.; Echavarren, Antonio M.

Authors

Javier Carreras

Madeleine Livendahl

Dr Paul Mcgonigal paul.mcgonigal@durham.ac.uk
Academic Visitor

Antonio M. Echavarren

Abstract

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.

Citation

Carreras, J., Livendahl, M., McGonigal, P. R., & Echavarren, A. M. (2014). Gold(I) as an Artificial Cyclase: Short Stereodivergent Syntheses of (−)-Epiglobulol and (−)-4β,7α- and (−)-4α,7α-Aromadendranediols. Angewandte Chemie International Edition, 53(19), 4896-4899. https://doi.org/10.1002/anie.201402044

Journal Article Type	Article
Acceptance Date	Feb 3, 2014
Online Publication Date	Apr 1, 2014
Publication Date	May 5, 2014
Deposit Date	Sep 14, 2015
Publicly Available Date	Jun 12, 2018
Journal	Angewandte Chemie International Edition
Print ISSN	1433-7851
Electronic ISSN	1521-3773
Publisher	Wiley
Peer Reviewed	Peer Reviewed
Volume	53
Issue	19
Pages	4896-4899
DOI	https://doi.org/10.1002/anie.201402044

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© 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.