Triarylethene compounds, including the well-known tamoxifene, have been widely studied and many synthetic pathway towards such compounds have been developed. Much less attention had been given to triarylethane compounds. Mostly, their application has been limited to substrates for control experiments or to model systems for studying rearrangement and migration phenomena. In the course of our synthetic attempts towards the preparation of quebecol, a promising polyphenolic compound found in maple syrup, we became interested in the construction of 1,2,2-triarylethane moieties. Two new strategies were explored to access this moiety via the construction of the associated 1,2,2-triarylethene scaffolds. The first one implies the addition of a diphenylmehtyl anion on a carbonyl compound. The second one uses a Corey-Fuchs / Suzuki-Miyaura sequence. Efficient conditions for the hydrogenation of 1,2,2-triarylethenes compounds to access the corresponding 1,2,2- triarylethanes were also investigated. This presentation will report successes and difficulties met while working on the construction of those moieties. The total synthesis of quebecol, using one of the developed approaches, will also be presented.

New approaches leading to 1,2,2-triarylethane and 1,2,2-triarylethene moieties: Application to the total synthesis of a polyphenoclic compound found in maple syrup

248th National Meeting (2014)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.