Total synthesis of (.+-.)-chelidonine

M Cushman, TC Choong, JT Valko…

Index: Cushman, Mark; Choong, Tung-Chung; Valko, Joseph T.; Koleck, Mary P. Journal of Organic Chemistry, 1980 , vol. 45, # 25 p. 5067 - 5073

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Citation Number: 86

Abstract

Condensation of the Schiff base 8 with 3, 4-(methy1enedioxy) 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 [l, 2-c] ...