Synthesis of melampolides and cis,cis-germacranolides as natural herbicide models |
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| Authors: | Francisco A Macías Raúl F Velasco Diego Castellano |
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| Institution: | a Grupo de Alelopatía, Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz, C/ República Saharaui s/n, Apdo. 40, 11510 Puerto Real (Cádiz), Spain
b Departamento de Química Física, Facultad de Ciencias, Universidad de Cádiz, C/ República Saharaui s/n, Apdo. 40, 11510 Puerto Real (Cádiz), Spain |
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| Abstract: | The comparative study between the theoretical molecular properties of the starting materials and the yields in the transformation of melampolides to cis,cis-germacranolides using SeO2/t-BuOOH (TBHP) as oxidant allows to establish a feasible relationship with their values of dipolar moment. Conditions for this transformation are optimized and some mechanistic considerations are made based in this finding. Cluster analysis of the phytotoxic activity of the melampolides and cis,cis-germacranolides obtained shows that the activity is greatly influenced by the spatial shape of the backbone, prevailing upon other factors such as the presence of reactive functional groups. |
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| Keywords: | Allylic oxidation mechanism Synthesis of sesquiterpenes Melampolides cis cis-Germacranolides Structure-activity relationship study (SAR) |
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