443688-01-5Relevant academic research and scientific papers
The isolation and synthesis of polyandrocarpamines A and B. Two new 2-aminoimidazolone compounds from the Fijian ascidian, Polyandrocarpa sp.
Davis, Rohan A,Aalbersberg, William,Meo, Semisi,Rocha, Rosana Moreira Da,Ireland, Chris M
, p. 3263 - 3269 (2007/10/03)
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.
