Synthesis of Substituted Quinolizidines via a Gold-Catalyzed Double Cyclization Cascade
Synthesis of Substituted Quinolizidines via a Gold-Catalyzed Double Cyclization Cascade
复制标题
通过金催化双环化级联合成取代的喹啉西啶
DOI：
10.1002/adsc.201500907
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发表时间：
2016
影响因子：
5.4
通讯作者：
H. Tokuyama
中科院分区：
文献类型：
--
作者：
S. Nonaka;K. Sugimoto;H. Ueda;H. Tokuyama
开发了一种通过阳离子金催化双环化级联合成喹诺西啶的新方法。该反应由金催化的烯酰胺的 6-外二环化引发，随后烯酰胺中间体进行第二次环化，得到相应的喹啉西啶衍生物。该反应的实用性通过应用于多取代喹西啶的合成和喹西啶生物碱（±）-羽扇豆碱的全合成得到了证明。
A novel synthesis of quinolizidines by a cationic gold‐catalyzed double cyclization cascade has been developed. The reaction was initiated by the gold‐catalyzed 6‐exo‐digcyclization of ynamides, which was followed by a second cyclization of an enamide intermediate to provide the corresponding quinolizidine derivatives. The utility of this reaction was demonstrated by application to the synthesis of multi‐substituted quinolizidines and by the total synthesis of a quinolizidine alkaloid, (±)‐lupinine.