Journal of Organic Chemistry p. 3953 - 3959 (1982)
Update date:2022-08-05
Topics:
Cannone, Persephone
Belanger, Denis
Lemay, Gilles
The reaction of bis(bromomagnesio)alkanes with bridged tricyclic endo- and exo-dicarboxylic anhydrides and their dihydro derivatives provides a general and versatile route to corresponding tricyclic spiro γ-butanolides.Futher extension of this methodology to the dianhydride of bicyclo<2.2.2>octene showed appreciable regioselectivity.The subsequent transformation of spiro γ-lactones into 4-spiro-2-butenolides by retro-Diels-Alder reaction has provided a simple and convenient synthesis of these molecules.Proton and 13C NMR spectra are reported for most of the compounds.
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