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Communication | Special issue | Vol 30, No. 1, 1990, pp.325-327
Published online, 1st January, 1970
DOI: 10.3987/COM-89-S55
Biomimetic Synthesis of Koumine by the Palladium-Catalyzed Intramolecular Coupling Reaction of 18-Hydroxytaberpsychine (18-Hydroxyanhydrovobasinediol)

Hiromitus Takayama, Mariko Kitajima, and Shin-ichiro Sakai*

*Faculty of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan


A principal Gelsemium alkaloid, koumine (1) was synthesized from 18-hydroxygardnutine (3) via the demethoxylation from the indole ring and the palladium-catalysed cyclization between C7 and C20 of the hypothetical biogenetic intermediate, 18-hydroxytaberpsychine (2).