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Note | Regular issue | Vol 63, No. 12, 2004, pp.2845-2850
Published online, 8th October, 2004
DOI: 10.3987/COM-04-10211
Synthesis of N1-Demethyl-20-deethylsuaveoline, the Structure Proposed for Sellowiine

Masashi Ohba* and Itaru Natsutani

*Advanced Science Research Center, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192, Japan

Abstract

A synthesis of Na-demethyl-20-deethylsuaveoline (1), the structure assigned to the Rauwolfia alkaloid sellowiine, has been accomplished for the first time through a route using intramolecular oxazole–olefin Diels–Alder reaction. The 1H- and 13C-NMR spectral data and the specific rotation of the synthetic 1 were in disagreement with those reported for a natural sample, leaving the chemistry of this alkaloid incomplete.