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Report | Regular issue | Vol 19, No. 4, 1982, pp.705-708
Published online, 1st January, 1970
DOI: 10.3987/R-1982-04-0705
Conversion of Ethyl Cincholoiponate into a Tricyclic Intermediate Adaptable to Chiral Syntheses of 10-Demethylated Alangium Alkaloids

Tozo Fujii, Masashi Ohba, and Hitoshi Suzuki

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


The title (—)-tricyclic amino ester VII has been synthesized by means of an initial condensation of 4-benzyloxy-3-methoxyphenacyl bromide with (+)-ethyl cincholoiponate (VIII) , derived from the Cinchona alkaloid cinchonine, and succeeding steps proceeding through the intermediates (+)-IX, X, XI, (—)-XIII, (—)-XIV, (+)-XV, (+)-XVI, (+)-XVII, and XVIII.