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Aucubin, a natural iridoid widely extracted from Aucuba japonica presents a strong interest as semisynthetic raw substantial, thanks to its numerous features. In this study, we describe an unprecedented reaction between trimethylsilyldiazomethane and the aldehyde-derived aucubin (3a) leading to different original non-natural skeletons exemplified by the tricyclic compounds 6 and 9 (Figure 1). The influence of catalysts, solvents and temperature on the formation of the products together with the hydrolysis of enoxysilane 4 will be presented.

Influence of solvents and catalysts on the formation and hydrolysis of polyfunctional enoxysilanes derived from aucubin