Assembly of the 1-azaspiro[5.5]undecane framework associated with perhydrohistrionicotoxin via electrocyclic ring-opening of a ring-fused gem -dichlorocyclopropane and trapping of the resulting π-allyl cation by a tethered, nitrogen-centered nucleop

Abstract

The carbamate-tethered gem-dichlorocyclopropane 27 was prepared, as a mixture of epimers, in ten steps from commercially available β,γ-unsaturated nitrile 9. Upon treatment with silver acetate under a range of reaction conditions, compound 27 underwent