Synthesis of na-demethyl-20-deethylsuaveoline,the structure proposed for sellowiine

摘要

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 ~1H-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.