6π-1-氮杂三烯电环化策略在海洋海绵代谢产物阿吉拉定A全合成中的应用及合成类似物的生物学评价

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.

作者信息

Meketa Matthew L, Weinreb Steven M, Nakao Yoichi, Fusetani Nobuhiro

机构信息

Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, USA.

出版信息

J Org Chem. 2007 Jun 22;72(13):4892-9. doi: 10.1021/jo0707232. Epub 2007 Jun 1.

DOI:10.1021/jo0707232

PMID:17539689

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.

摘要

报道了血管生成抑制性海洋代谢产物ageladine A的12步合成方法。关键步骤包括用于形成吡啶环的6π-1-氮杂三烯电环化反应以及N-Boc-吡咯-2-硼酸与氯代咪唑并吡啶的铃木-宫浦偶联反应。此外，还描述了在此合成过程中制备的各种ageladine A合成类似物的生物活性评估。