Morgane Gaydou, PhD student under the supervision of Prof. Antonio M. Echavarren, has defended her PhD Thesis entitled “Gold(I)-Catalyzed Cyclizations and Enantioselective Total Synthesis of (+)-Schisanwilsonene A” (assigned to the Organic and Analytical Chemistry Department of the Universitat Rovira i Virgili) publicly on October 14th at the ICIQ auditorium.
The members of her evaluation committee were: Prof. Jose Manuel González (Universidad de Oviedo), Prof. Igor Larrosa (University of Manchester) and Prof. Paolo Melchiorre (ICIQ).
Gold(I)-catalyzed activation of alkynes followed by nucleophilic attack have been extensively studied in our group. In this work, the developpement of a new reaction catalyzed by Au (I) using trimethylsilyl azide and alkynes leading to the formation of tetrazoles is first established. Then, the intermolecular trapping of the in situ formed Au (I)-carbenes with different novel nucleophiles is described. Finally, the 1,5-migration reaction of 1,6-enynes catalyzed by Au (I) is applied to the synthesis of the natural products (+)-schisanwilsonene A, B and C which possess interesting biological activity against hepatitis B.