The Journal of Organic Chemistry

Alkaloids of Thalictrum. 28. The structure of thalibrunine, a reinvestigation and revision

J Wu, JL Beal, RW Doskotch

Index: Wu, Jinn; Beal, Jack L.; Doskotch, Raymond W. Journal of Organic Chemistry, 1980 , vol. 45, # 2 p. 208 - 212

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Citation Number: 13

Abstract

Evidence is presented that thalibrunine has structure 2 and is the 2'-hydroxy derivative of hernandezine. Ceric ammonium nitrate oxidation of thalibrunine acetate (3) gave 2-methoxy- 4-acetoxy-4', 5-diformyldiphenyl ether (6), which was also prepared synthetically from 2- methoxy-4-(benzyloxy) phenol and 4-bromobenzaldehyde in four steps, thereby firmly establishing the tail-to-tail diphenyl ether unit. Anomalous products, o-cresol 14 and ...