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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Transformations_of_the_2,7-Seco_Aspidosperma_Alkaloid_Leuconolam,Structure_Revision_of_epi-Leuconolam,_and_Partial_Syntheses_of_Leuconoxine_and_Leuconodines_A_and_F.pdf - Published Version Restricted to Repository staff only Download (2MB) | Request a copy |
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 |
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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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