CONICET | Buscador de Institutos y Recursos Humanos

Natural products (NP) are an important and essential source for research and discovery of new therapeutic agents.1 They have very different chemical properties from most synthetic compounds, which is why they are currently used as chemical precursors to obtain a wide variety of compounds with molecular diversity (structural and chemical). To this end, one of the strategies used, called Complexity to Diversity,2 focuses on obtaining compounds through changes in the ring system, generating drastic modifications in the derivatives with each other and with the parent compound. Ring distortion reactions can be carried out by conventional chemoselective reactions using common, inexpensive, versatile, easy to handle and accessible reagents. Another useful and environmentally friendly methodology is based on the use of enzymes through chemo- and stereoselective reactions. This synthetic strategy makes it possible to reduce the energy required in conventional chemical reactions and minimize the generation of secondary products that are harmful to the environment, by using eco-friendly solvents, non-toxic and non-polluting reagents. 3In this work, ring distortion reactions were performed in solidagenone (Sol), a diterpene isolated from Solidago chilensis Meyen, in order to obtain structural derivatives through two ring distortion reaction methodologies. Method A was based on structural rearrangements in oxidative peroxide medium using standard chemistry.4 Similarly, method B, is a chemoenzymatic oxidative transformation using lipase/H2O2 and ethyl acetate, for selectively oxidize and further condense furan moiety. 5 In addition, in order to compare the results obtained, this proposal was extended to another diterpene from the same vegetal material, Junceic Acid (JA). The structural diversity obtained in this library of compounds was evaluated by Tanimoto similarity coefficient analysis.