54707-47-0Relevant academic research and scientific papers
One-step synthesis of furan rings from α-isopropylidene ketones mediated by iodine/DMSO: An approach to potent bioactive terpenes
Salihila, Jonida,Silva, Lúcia,Pérez Del Pulgar, Helena,Quílez Molina, Ana,González-Coloma, Azucena,Olmeda, A. Sonia,Quílez Del Moral, José F.,Barrero, Alejandro F.
, p. 6886 - 6894 (2019/06/14)
The system I2/dimethyl sulfoxide mediates the one-step transformation of α-isopropylidene ketones into furan rings following a biomimetic approach. This methodology has been used for the synthesis of terpene furans such as mintfurane, curzerene, atractylon, and isoatractylon, all of them possessing interesting biological activities. The synthesis of linderazulene directly from 4,5-epoxygermacrone via a cascade reaction shows the potential of this protocol. Additionally, this compound proved to show significant ixodicidal activity.
Structural diversity from the transannular cyclizations of natural germacrone and epoxy derivatives: A theoretical-experimental study
Pérez Morales, M. Carmen,Catalán, Julieta V.,Domingo, Victoriano,Jaraíz, Martín,Herrador, M. Mar,Quílez Del Moral, José F.,L?pez-Pérez, José-Luis,Barrero, Alejandro F.
supporting information, p. 6598 - 6612 (2013/06/27)
Treatment of germacrone (1) with different electrophiles, and of its epoxy derivatives germacrone-4,5-epoxide (2), germacrone-1,10-epoxide (3) and isogermacrone-4,5-epoxide (4) with Br?nsted/Lewis acids and Ti III, gives rise to a great structural diversity. Thus, by using a maximum of two steps, the production of more than 40 compounds corresponding to 14 skeletons is described. Computational calculations rationalizing the structural divergence produced are also described. Finally, since some of the compounds generated are bioactive natural sesquiterpenes, the mechanisms of formation of these substances will provide new insights in their biosynthesis. Copyright
