Author/Authors :
Forni، نويسنده , , Eleonora and Cipolla، نويسنده , , Laura and Caneva، نويسنده , , Enrico and La Ferla، نويسنده , , Barbara and Peri، نويسنده , , Francesco and Nicotra، نويسنده , , Francesco، نويسنده ,
Abstract :
Iodocyclisation of polybenzylated allyl α-C-fructofuranoside 1 afforded the bicyclic iodoether 2 through debenzylation at C-1; treatment of 2 with zinc and acetic acid restored the allylic group with concomitant deprotection of the hydroxyl group at C-1, which was oxidised to the corresponding aldehyde 4. Reaction of 4 with vinylmagnesium bromide afforded diene 5, whose double bonds were reacted regioselectively in order to obtain, upon iodocyclisation under different experimental conditions, bicycles 6 or 7, or tricycle 8.
