Transformations of the 2,7-Seco aspidosperma alkaloid leuconolam, structure revision of epi-Leuconolam, and partial syntheses of leuconoxine and leuconodines A and F

Kam, T.S. and Low, Y.Y. and Hong, F.J. and Lim, K.H. and Thomas, N.F. (2013) Transformations of the 2,7-Seco aspidosperma alkaloid leuconolam, structure revision of epi-Leuconolam, and partial syntheses of leuconoxine and leuconodines A and F. Journal of Natural Products, 77 (2). pp. 327-338. ISSN 0163-3864, DOI https://doi.org/10.1021/np400922x.

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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.

Item Type: Article
Funders: UNSPECIFIED
Additional Information: Department of Chemistry, Faculty of Science, University of Malaya
Uncontrolled Keywords: Seco Aspidosperma Alkaloid Leuconolam; Leuconoxine and Leuconodines; Molecular bromine.
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Science > Department of Chemistry
Depositing User: Ms. Suhaila Syakila Alby
Date Deposited: 31 Oct 2014 03:02
Last Modified: 31 Oct 2014 03:02
URI: http://eprints.um.edu.my/id/eprint/10379

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