Synthesis of (-)-Cannabimovone and Structural Reassignment of Anhydrocannabimovone through Gold(I)-Catalyzed Cycloisomerization

Javier Carreras; Mariia S Kirillova; Antonio M Echavarren

doi:10.1002/anie.201601834

Synthesis of (-)-Cannabimovone and Structural Reassignment of Anhydrocannabimovone through Gold(I)-Catalyzed Cycloisomerization

Angew Chem Int Ed Engl. 2016 Jun 13;55(25):7121-5. doi: 10.1002/anie.201601834. Epub 2016 Apr 27.

Authors

Javier Carreras¹, Mariia S Kirillova¹, Antonio M Echavarren^{2

3}

Affiliations

¹ Institute of Chemical Research of Catalonia (ICIQ), Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007, Tarragona, Spain.
² Institute of Chemical Research of Catalonia (ICIQ), Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007, Tarragona, Spain. aechavarren@iciq.es.
³ Departament de Química Analítica i Química, Orgànica, Universitat Rovira i Virgili, C/ Marcel⋅li Domingo s/n, 43007, Tarragona, Spain. aechavarren@iciq.es.

Abstract

The first total synthesis of cannabimovone from Cannabis sativa and anhydrocannabimovone was achieved by means of a highly stereoselective gold(I)-catalyzed cycloisomerization. The results led to reassignment of the structure of anhydrocannabimovone.

Keywords: cannabinoids; cycloisomerization; gold; oxy-Michael reaction; total synthesis.

Publication types

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