Abstract
For the purpose of synthetic approaches toward colchicine (2) from O-methylandrocymbine (1a), reaction of homomorphinandienones (1a, b) was carried out. Oxidation of 1a, b with 35% aqueous hydrogen peroxide gave a separable diastereomeric mixture of N-oxides (5, 6). Polonovski reaction of the N-oxides (5) with acetic anhydride in CH 2 Cl 2 afforded N-demethyl-N-acetamide (7a), whereas that of 5 and 6 with acetic anhydride in the presence of triethylamine gave enamines (8a, b) together with N-demethyl-N-acetamides (7a, b). Furthermore, reaction of enamines (8a, b) with N-bromosuccinimide in dimethoxyethane-H 2 O or methanol produced α-bromo amides (9a, b)
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