No abstract

The reaction of N-tosyl-2-pyridinone with tert-butyldimethylsilyl ketene acetal, catalyzed by a Lewis acid, has been investigated. While both the C-4 Michael adduct 3 and the bicyclic compound 5 were isolated from aluminum chloride-or trimethylaluminum-catalyzed reactions, the former was afforded as the sole product from diethylaluminum chloride-or trimethylsilyl trifluoromethanesulfonate-catalyzed reactions. During investigation of a synthesis of corynantheidol, a method for construction of the key intermediate 30 was accomplished via, (1), the efficient conversion of the enamine moiety to an alkenyl bromide (20 22), followed by the Sonogashira coupling reduction (22 23); (2), selective reduction of the acetylene and intramolecular cyclization (25 26); (3), the coupling reaction with the indole unit (27 30).

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