71748-66-8Relevant articles and documents
Synthesis of melampolides and cis,cis-germacranolides as natural herbicide models
Macías, Francisco A.,Velasco, Raúl F.,álvarez, José A.,Castellano, Diego,Galindo, Juan C.G.
, p. 8477 - 8488 (2004)
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. Graphical abstract.
Chemistry of costunolide and biological activity of the derived lactones
Kalsi,Khurana, Sarita,Talwar
, p. 103 - 109 (2007/10/02)
Costunolide and its derived C-16 germacranolides on oxidation with selenium dioxide-t-butyl hydroperoxide afforded two melampolides, an aldehydolactone and the corresponding hydroxylactone, in each case. Structures were assigned to these melampolides on the basis of spectral data and chemical correlation. The aldehydolactones were significantly more active root promotors than their parent lactones. Costunolide and related germacranolides underwent cyclization on treatment with iodine and pyridinium chlorochromate to afford interesting products. (-)-β-Frullanolide has been synthesized and shown to be biologically more active when compared with its parent trans-lactone.
