布朗斯特酸催化的高度立体选择性芳烃-烯酰胺环化反应。（±）-去溴树状菌素A和C全合成中的一种新型烯酮亚胺鎓皮克特-施彭格勒环化反应。
Brønsted acid-catalyzed highly stereoselective arene-ynamide cyclizations. A novel keteniminium Pictet-Spengler cyclization in total syntheses of (+/-)-desbromoarborescidines A and C.
作者信息
Zhang Yanshi, Hsung Richard P, Zhang Xuejun, Huang Jian, Slafer Brian W, Davis Allison
机构信息
Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, USA.
出版信息
Org Lett. 2005 Mar 17;7(6):1047-50. doi: 10.1021/ol0473391.
PMID:15760135
Abstract
[reaction: see text] A Brønsted acid-catalyzed highly stereoselective arene-ynamide cyclization is described. These reactions constitute a keteniminium variant of Pictet-Spengler cyclizations, leading to efficient synthesis of nitrogen heterocycles and related alkaloids. Total syntheses of desbromoarborescidines A and C are illustrated here as first applications of this methodology.
摘要
[反应：见正文] 描述了一种布朗斯特酸催化的高度立体选择性芳烃-烯炔酰胺环化反应。这些反应构成了皮克特-施彭格勒环化反应的烯酮亚胺变体，可高效合成含氮杂环化合物及相关生物碱。本文展示了去溴树碱A和C的全合成，作为该方法的首次应用。
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