一种利用从3-羟基黄酮衍生的氧化吡啶鎓的光生作用来合成rocaglamides的仿生方法。
A biomimetic approach to the rocaglamides employing photogeneration of oxidopyryliums derived from 3-hydroxyflavones.
作者信息
Gerard Baudouin, Jones Ii Guilford, Porco John A
机构信息
Department of Chemistry, Center for Chemical Methodology and Library Development, Boston University, Boston, Massachusetts 02215, USA.
出版信息
J Am Chem Soc. 2004 Oct 27;126(42):13620-1. doi: 10.1021/ja044798o.
A unified biomimetic approach to the aglain-forbaglin-rocaglamide classes of natural products is reported. The approach involves photogeneration of oxidopyryliums via excited-state intramolecular proton transfer (ESIPT) of 3-hydroxyflavones followed by [3+2] dipolar cycloaddition to the aglain core. An alpha-ketol (acyloin) rearrangement was employed to transform the aglain core to the rocaglamide framework. This approach was successfully used for the synthesis of the natural product (+/-)-methyl rocaglate.
报道了一种用于天然产物阿格拉因、福贝格灵和罗卡酰胺类化合物的统一仿生方法。该方法包括通过3-羟基黄酮的激发态分子内质子转移（ESIPT）光生成氧化吡啶鎓，然后与阿格拉因核心进行[3+2]偶极环加成。采用α-酮醇（偶姻）重排将阿格拉因核心转化为罗卡酰胺骨架。该方法成功用于天然产物（±）-甲基罗卡酯的合成。
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