Transformations of the 2,7-Seco aspidosperma alkaloid leuconolam, structure revision of epi-Leuconolam, and partial syntheses of leuconoxine and leuconodines A and F
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 pro...
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| Format: | Article |
| Language: | English |
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American Chemical Society
2013
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| Online Access: | http://eprints.um.edu.my/10379/1/Transformations_of_the_2%2C7-Seco_Aspidosperma_Alkaloid_Leuconolam%2CStructure_Revision_of_epi-Leuconolam%2C_and_Partial_Syntheses_of_Leuconoxine_and_Leuconodines_A_and_F.pdf |
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| author | Kam, T.S. Low, Y.Y. Hong, F.J. Lim, K.H. Thomas, N.F. |
| author_facet | Kam, T.S. Low, Y.Y. Hong, F.J. Lim, K.H. Thomas, N.F. |
| author_sort | Kam, T.S. |
| collection | UM |
| description | 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. |
| first_indexed | 2024-03-06T05:26:00Z |
| format | Article |
| id | um.eprints-10379 |
| institution | Universiti Malaya |
| language | English |
| last_indexed | 2024-03-06T05:26:00Z |
| publishDate | 2013 |
| publisher | American Chemical Society |
| record_format | dspace |
| spelling | um.eprints-103792014-10-31T03:02:55Z http://eprints.um.edu.my/10379/ 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. Low, Y.Y. Hong, F.J. Lim, K.H. Thomas, N.F. QD Chemistry 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. American Chemical Society 2013 Article PeerReviewed application/pdf en http://eprints.um.edu.my/10379/1/Transformations_of_the_2%2C7-Seco_Aspidosperma_Alkaloid_Leuconolam%2CStructure_Revision_of_epi-Leuconolam%2C_and_Partial_Syntheses_of_Leuconoxine_and_Leuconodines_A_and_F.pdf 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 <https://doi.org/10.1021/np400922x>. DOI: 10.1021/np400922x |
| spellingShingle | QD Chemistry Kam, T.S. Low, Y.Y. Hong, F.J. Lim, K.H. Thomas, N.F. Transformations of the 2,7-Seco aspidosperma alkaloid leuconolam, structure revision of epi-Leuconolam, and partial syntheses of leuconoxine and leuconodines A and F |
| title | Transformations of the 2,7-Seco aspidosperma alkaloid leuconolam, structure revision of epi-Leuconolam, and partial syntheses of leuconoxine and leuconodines A and F |
| title_full | Transformations of the 2,7-Seco aspidosperma alkaloid leuconolam, structure revision of epi-Leuconolam, and partial syntheses of leuconoxine and leuconodines A and F |
| title_fullStr | Transformations of the 2,7-Seco aspidosperma alkaloid leuconolam, structure revision of epi-Leuconolam, and partial syntheses of leuconoxine and leuconodines A and F |
| title_full_unstemmed | Transformations of the 2,7-Seco aspidosperma alkaloid leuconolam, structure revision of epi-Leuconolam, and partial syntheses of leuconoxine and leuconodines A and F |
| title_short | Transformations of the 2,7-Seco aspidosperma alkaloid leuconolam, structure revision of epi-Leuconolam, and partial syntheses of leuconoxine and leuconodines A and F |
| title_sort | transformations of the 2 7 seco aspidosperma alkaloid leuconolam structure revision of epi leuconolam and partial syntheses of leuconoxine and leuconodines a and f |
| topic | QD Chemistry |
| url | http://eprints.um.edu.my/10379/1/Transformations_of_the_2%2C7-Seco_Aspidosperma_Alkaloid_Leuconolam%2CStructure_Revision_of_epi-Leuconolam%2C_and_Partial_Syntheses_of_Leuconoxine_and_Leuconodines_A_and_F.pdf |
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