钯催化的乌尔曼交叉偶联/串联还原环化反应路线合成乌灵碱生物碱家族的关键成员
Palladium-Catalyzed Ullmann Cross-Coupling/Tandem Reductive Cyclization Route to Key Members of the Uleine Alkaloid Family.
作者信息
Tang Fei, Banwell Martin G, Willis Anthony C
机构信息
Research School of Chemistry, Institute of Advanced Studies, The Australian National University , Canberra, ACT 2601, Australia.
出版信息
J Org Chem. 2016 Apr 1;81(7):2950-7. doi: 10.1021/acs.joc.6b00240. Epub 2016 Mar 17.
The trisubstituted cyclohexenone 12, generated through a palladium-catalyzed Ullmann cross-coupling reaction between o-iodonitrobenzene and a 4,5-trans-disubstituted 2-iodo-2-cyclohexen-1-one, engaged in a tandem reductive cyclization process upon exposure to hydrogen gas in the presence of Raney cobalt. As a result, the 1,5-methanoazocino[4,3-b]indole 13 was obtained and this could be readily elaborated to the racemic modifications of the alkaloids uleine, dasycarpidone, noruleine, and nordasycarpidone (1-4, respectively).
通过邻碘硝基苯与4,5-反式二取代的2-碘-2-环己烯-1-酮之间的钯催化乌尔曼交叉偶联反应生成的三取代环己烯酮12，在阮内钴存在下暴露于氢气时进行串联还原环化过程。结果，得到了1,5-亚甲基氮杂环辛并[4,3-b]吲哚13，并且可以很容易地将其转化为生物碱乌来碱、达西卡匹酮、去甲乌来碱和去甲达西卡匹酮（分别为1-4）的外消旋变体。
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