106471-49-2Relevant academic research and scientific papers
BF3-Catalyzed Cycloadditions of Naturally Occuring Sesquiterpene p-Benzoquinones
Joseph-Nathan, Pedro,Garibay, Maria E.,Santillan, Rosa L.
, p. 759 - 763 (2007/10/02)
Lewis acid catalyzed reactions of all known naturally occurring perezone analogues and two allylic alcohols prepared from perezone and hydroxyperezone show that these p-benzoquinones exhibit a complex behavior upon acid treatment.As in the case of perezone, O-angeloylperezone and 6-angeloxyperezone afforded pipitzol analogues.Hydroxyperezone and O-angeloyl-6-hydroxyperezone yielded a stable boron adduct of perezinone.Curcuquinone, the simplest sesquiterpene quinone, afforded mainly polymeric material, while 15-hydroxyperezone and hydroxyperezone derivatives gave a dibenzofurandione and a tricyclic molecule containing a new skeleton, respectively.The results for O-angeloylperezone, compared with those of perezone, show that steric effects play an important role in these transformation allowing at present complete stereocontrol of the reaction outcome.
