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Report | Regular issue | Vol 24, No. 2, 1986, pp.345-347
Published online, 1st January, 1970
DOI: 10.3987/R-1986-02-0345
Racemic and Chiral Syntheses of the Alangium Alkaloid Alancine

Tozo Fujii,* Masashi Ohba, Asako Yonezawa, Jun Sakaguchi, Sunil K. Chattopadhyay, David J. Slatkin, Paul L. Schiff, Jr., and Anli B. Ray

*Faculty of Pharmaceutical Scicences, Kanazawa University, 13-1 Takara-machi, Kanazawa 920-0934, Japan


(±)-Alancine [(±)-I] has been synthesized in good yield from the tricyclic amino acid (±)-V by catalytic hydrogenolysis. Treatment of (±)-I with aqueous HCl gave the hydrochloride salt (±)-I·HCl. A parallel synthesis starting with (-)-V produced (-) -alancine [(-)-I] as well as its hydrochloride (-) -I·HCl in good yields. The synthetic (-)-I·HCl was found to be identical with a sample isolated from Alangium lamarckii Thw.