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.

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