Journal of Organic Chemistry p. 5067 - 5073 (1980)
Update date:2022-08-29
Topics:
Cushman, Mark
Choong, Tung-Chung
Valko, Joseph T.
Koleck, Mary P.
Condensation of the Schiff base 8 with 3,4-(methylenedioxy)homophthalic anhydride (13) was exploited as the key step in a total synthesis of the benzophenanthridine alkaloid (+/-)-chelidonine (1).A variety of reaction conditions were investigated in order to maximize the production of the desired thermodynamically less stable cis diastereomer.A method was devised for the conversion of 24 to its acid chloride without production of the indeno<1,2-c>isoquinoline 30.The migration of an aromatic ring was observed on treatment of the diazo ketone 26 with acid.This reaction is reminiscent of the Hayashi rearrangement.
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