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. © 2002 Elsevier Science Ltd. All rights reserved.
Forni, E., Cipolla, L., Caneva, E., LA FERLA, B., Peri, F., Nicotra, F. (2002). Polycyclic Scaffolds from Fructose. TETRAHEDRON LETTERS, 43(7), 1355-1357 [10.1016/S0040-4039(01)02393-0].
Polycyclic Scaffolds from Fructose
CIPOLLA, LAURA FRANCESCA;LA FERLA, BARBARA;PERI, FRANCESCO;NICOTRA, FRANCESCO
2002
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. © 2002 Elsevier Science Ltd. All rights reserved.
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