Re-functionalisation of α-substituted isocolchicides via nucleophilic tele-substitution
Abstract
9-Methoxyisocolchicide 1 in excess methanethiolate–methanol, or Me2SO, slowly undergoes ipso-substitution giving 9-methylthioisocolchicide 3, which then suffers tele-substitution giving 11-methylthioisocolchicide 2; this activation by dicoordinated sulfur is used for amino re-functionalisation of the isocolchicide system.