Application of a 6π-1-azatriene electrocyclization strategy to the total synthesis of the marine sponge metabolite ageladine A and biological evaluation of synthetic …

…, SM Weinreb, Y Nakao, N Fusetani

Index: Meketa, Matthew L.; Weinreb, Steven M.; Nakao, Yoichi; Fusetani, Nobuhiro Journal of Organic Chemistry, 2007 , vol. 72, # 13 p. 4892 - 4899

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Citation Number: 34

Abstract

A 12-step synthesis of the angiogenesis inhibitory marine metabolite ageladine A is reported. The key steps include a 6π-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.