Davis, R.A. and Aalbersberg, William G.L. and Meo, Semisi V. and Moneira da Rocha, R. and Ireland, C.M. (2002) The isolation and synthesis of polyandrocarpamines A and B. Two new 2-aminoimidazolone compounds from the Fijian ascidian, Polyandrocarpa sp. Tetrahedron, 58 (16). pp. 3263-3269. ISSN 0040-4020
Full text not available from this repository.Abstract
Chemical investigation of a Fijian ascidian, Polyandrocarpa sp., has resulted in the isolation of two new 2-aminoimidazolone-derived compounds, polyandrocarpamines A (1) and B (2). The structures of these unique metabolites were determined by the interpretation of spectroscopic data and confirmed by total synthesis. The stereospecific synthesis of 1 was accomplished using aldol condensation chemistry to generate an arylidene thiohydantoin that was subsequently transaminated to yield polyandrocarpamine A. Demethylation of synthetic 1 afforded polyandrocarpamine B. Both the natural product and synthetic polyandrocarpamines were assigned Z geometries about the exocyclic double bond (C-5/C-7) on the basis of 13C/1H long-range coupling constants, which were measured using a gHSQMBC experiment.
| Item Type: | Journal Article |
|---|---|
| Subjects: | Q Science > QD Chemistry |
| Divisions: | Faculty of Science, Technology and Environment (FSTE) > Institute of Applied Science |
| Depositing User: | Ms Shalni Sanjana |
| Date Deposited: | 07 Aug 2002 23:20 |
| Last Modified: | 07 Aug 2012 23:20 |
| URI: | https://repository.usp.ac.fj/id/eprint/5061 |
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