通过2-氨基丙烯醛环加成反应全合成（±）束丝菌素。
Total synthesis of (+/-)fasicularin via a 2-amidoacrolein cycloaddition.
作者信息
Maeng Jun-Ho, Funk Raymond L
机构信息
Department of Chemistry, Pennsylvania State University, University Park, PA 16802, USA.
出版信息
Org Lett. 2002 Feb 7;4(3):331-3. doi: 10.1021/ol016850g.
The total synthesis of the cytotoxin fasicularin is described. The key steps include the following: (1) an intermolecular Diels-Alder cycloaddition of a 2-(triflamido)acrolein with the dioxolane ketal of trideca-1,3-dien-7-one to establish the trans-perhydroisoquinoline stereochemistry, (2) a stereoelectronically controlled hydride addition to a N(1)-C(2) iminium ion to introduce the equatorial hexyl substituent, and (3) elaboration of the pyrido ring by an internal aldol reaction.
描述了细胞毒素束丝藻毒素的全合成。关键步骤如下：(1) 2-(三氟甲酰胺基)丙烯醛与十三碳-1,3-二烯-7-酮的二氧戊环缩酮进行分子间狄尔斯-阿尔德环加成反应，以确立反式全氢异喹啉立体化学；(2) 对N(1)-C(2)亚胺离子进行立体电子控制的氢化物加成反应，以引入赤道面的己基取代基；(3) 通过分子内羟醛反应构建吡啶环。
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