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Paper | Regular issue | Vol 45, No. 4, 1997, pp.779-786
Published online, 1st January, 1970
DOI: 10.3987/COM-97-7752
Synthesis of (±)-Cathenamine and (±)-19-Epicathenamine, Isolated as Their C-21α-Cyano Derivatives

Mauri Lounasmaa,* Reija Jokela, Pirjo Hanhinen, and Ulla Anttila

*Laboratory for Organic and Bioorganic Chemistry, Technical University of Helsinki, P.O. Box 6100, FIN-02150 HUT Espoo, Finland


A short synthetic route from the easily accessible O-Boc-Z-geissoschizine (2a) to (±)-cathenamine (3) and (±)-19-epicathenamine (4) is presented. Both compounds, which are important biogenetic intermediates in the formation of heteroyohimbine alkaloids, were isolated as their synthetic equivalents, (±)-21α-cyanotetrahydroalstonine (5) and (±)-21α-cyano-19-epiajmalicine (6), respectively.