Application of a 6pi-1-azatriene electrocyclization strategy to the total synthesis of the marine sponge metabolite ageladine A and biological evaluation of synthetic analogues |
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| Authors: | Meketa Matthew L Weinreb Steven M Nakao Yoichi Fusetani Nobuhiro |
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| Institution: | Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, USA. |
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| Abstract: | A 12-step synthesis of the angiogenesis inhibitory marine metabolite ageladine A is reported. The key steps include a 6pi-1-azatriene electrocyclization for formation of the pyridine ring and a Suzuki-Miyaura coupling of N-Boc-pyrrole-2-boronic acid with a chloroimidazopyridine. In addition, an assessment of the biological activity of a variety of synthetic analogues of ageladine A prepared during this synthesis is described. |
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