Structure and stereochemistry of ankorine: A total synthesis of (±)-ankorine

✍ Scribed by Tozo Fujii; Shigeyuki Yoshifuji; Koichiro Yamada

• Publisher: Elsevier Science
• Year: 1975
• Tongue: French
• Weight: 211 KB
• Volume: 16
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)72188-5

✦ Synopsis

Ankorine is one of the Alangium lamarckii alkaloids "' structurally related to the Ipecac alkaloids, e.. , emetine (I),' and has been assigned the plane structure II largely on the basis of physical measurements .' However, neither the precise location of the phenolic hydroxyl group nor the stereochemistry of this alkaloid was established at that time. The recent communication by Szbntay et a1.4 of the synthesis of four possible racemic stereoisomers of II suggested that the phenol function of ankorine must be placed at an alternative position (structure III). Now we wish to record the results of our own synthetic effort, which have proved that structure IV is a complete expression, apart from its absolute configuration, for ankorine .