A six-step total synthesis of α-thujone and d6-α-thujone, enabling facile access to isotopically labelled metabolites

Irene Thamm; Johannes Richers; Michael Rychlik; Konrad Tiefenbacher

doi:10.1039/c6cc05376a

A six-step total synthesis of α-thujone and d₆-α-thujone, enabling facile access to isotopically labelled metabolites

Chem Commun (Camb). 2016 Sep 22;52(78):11701-11703. doi: 10.1039/c6cc05376a.

Authors

Irene Thamm¹, Johannes Richers², Michael Rychlik¹, Konrad Tiefenbacher³

Affiliations

¹ Analytical Food Chemistry, Technische Universität München, Alte Akademie 10, 85354 Freising, Germany.
² Department of Chemistry, Technische Universität München, Lichtenbergstraße 4, 85747 Garching, Germany.
³ Department of Chemistry, University of Basel, St. Johannsring 19, CH-4056 Basel, Switzerland. konrad.tiefenbacher@unibas.ch and Department of Biosystems Science and Engineering, ETH Zürich, Mattenstrasse 26, CH-4058 Basel, Switzerland. tkonrad@ethz.ch.

PMID: 27709180
DOI: 10.1039/c6cc05376a

Abstract

The short synthesis of α-thujone relies on the functionalization of the readily available dimethylfulvene. Furthermore, the three main metabolites of the natural product were also synthesized. Since d₆-acetone can be used as a starting material, the route developed allows for the facile incorporation of isotopic labels which are required for detecting and quantifying trace amounts via GC/MS analysis.