Synthesis of Na-Demethyl-20- deethylsuaveoline, the Struc- ture Proposed for Sellowiine

A synthesis of N a -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 1 H-and 13 C-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.