Variations on radical cascades of vinyl radicals generated from bromomethyldimethylsilyl propargyl ethers

Article abstract of DOI:10.1016/0040-4020(96)00634-5

Vinyl radicals generated from bromomethyldimethylsilyl propargyl ethers have been efficiently engaged in cascades of radical cyclizations. Through the enchainment of 5-exo-dig-5-(π-endo)-exo-trig-6-endo-trig or 5-exo-dig-5-(π-endo)-exo-trig-6-exo-trig radical processes, hydrindene and a steroid skeleton could be assembled. Appending on the alkyne a suitable chain bearing a dioxolane for 1,5-radical translocations proved also very rewarding since a very diasteroselective access to cyclopentanone derivatives could be devised.