Electrocyclic Ring-Opening/p-Allyl Cation Cyclization Reaction Sequences Involving gem-Dihalocyclopropanes as Substrates: Application to Syntheses of (+)-, (+)-, and (-)-g-Lycorane

Banwell, Martin; Harvey, Joanne; Hockless, David; Wu, Angela W

Electrocyclic Ring-Opening/p-Allyl Cation Cyclization Reaction Sequences Involving gem-Dihalocyclopropanes as Substrates: Application to Syntheses of (+)-, (+)-, and (-)-g-Lycorane

Date

2000

Authors

Banwell, Martin

Harvey, Joanne

Hockless, David

Wu, Angela W

Publisher

American Chemical Society

Abstract

The readily prepared gem-dibromocyclopropanes (±)-13 and (±)-19 each engage in a silver(I)-promoted electrocyclic ring-opening/π-allyl cation cyclization sequence to deliver the hexahydroindole (±)-20, which participates in a Suzuki cross-coupling rea