Total Synthesis of a Dimeric Thymol Derivative Isolated from Arnica sachalinensis

Irene De Silvestro; Samuel L Drew; Gary S Nichol; Fernanda Duarte; Andrew L Lawrence

doi:10.1002/anie.201701481

Total Synthesis of a Dimeric Thymol Derivative Isolated from Arnica sachalinensis

Angew Chem Int Ed Engl. 2017 Jun 6;56(24):6813-6817. doi: 10.1002/anie.201701481. Epub 2017 May 5.

Authors

Irene De Silvestro¹, Samuel L Drew^{2

3}, Gary S Nichol¹, Fernanda Duarte¹, Andrew L Lawrence¹

Affiliations

¹ EaStCHEM School of Chemistry, University of Edinburgh, Joseph Black Building, David Brewster Road, Edinburgh, EH9 3FJ, UK.
² Research School of Chemistry, Australian National University, Canberra, ACT, 2601, Australia.
³ Present address: Department of Chemistry, University of California, Irvine, CA, 92697-2025, USA.

PMID: 28474807
DOI: 10.1002/anie.201701481

Abstract

The total synthesis of a dimeric thymol derivative (thymarnicol) isolated from Arnica sachalinensis was accomplished in 6 steps. A key biomimetic Diels-Alder dimerization was found to occur at ambient temperature and the final oxidative cyclization occurs when the substrate is exposed to air and visible light. These results indicate that this natural product is likely the result of spontaneous (non-enzyme-mediated) reactivity.

Keywords: biomimetic synthesis; cycloaddition; dimerization; natural products; terpenoids.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Arnica / chemistry*
Biological Products / chemistry
Biomimetics
Chromatography, High Pressure Liquid
Crystallography, X-Ray
Cyclization
Density Functional Theory
Dimerization
Feasibility Studies
Light
Molecular Structure
Oxidation-Reduction
Proton Magnetic Resonance Spectroscopy
Thymol / analogs & derivatives*

Substances

Biological Products
Thymol