Document Type
Article (Restricted)
Publication Date
1-1-2013
Abstract
Several transformations of the seco Aspidosperma alkaloid leuconolam were carried out. The based-induced reaction resulted in cyclization to yield two epimers, the major product corresponding to the optical antipode of a (+)-meloscine derivative. The structures and relative configuration of the products were confirmed by X-ray diffraction analysis. Reaction of leuconolam and epileuconolam with various acids, molecular bromine, and hydrogen gave results that indicated that the structure of the alkaloid, previously assigned as epi-leuconolam,was incorrect. This was confirmed by an X-ray diffraction analysis, which revealed that epi-leuconolam is in fact 6,7-dehydroleuconoxine. Short partial syntheses of the diazaspiro indole alkaloid leuconoxine and the new leuconoxine-type alkaloids leuconodines A and F were carried out.
Keywords
Seco Aspidosperma Alkaloid Leuconolam, Leuconoxine and Leuconodines, Molecular bromine.
Divisions
CHEMISTRY
Publication Title
Journal of Natural Products
Volume
77
Issue
2
Publisher
American Chemical Society
Additional Information
Department of Chemistry, Faculty of Science, University of Malaya