A mild and efficient synthesis of oxindoles: Progress towards the synthesis of welwitindolinone a isonitrile

被引:71
作者
Ready, JM [1 ]
Reisman, SE [1 ]
Hirata, M [1 ]
Weiss, MM [1 ]
Tamaki, K [1 ]
Ovaska, TV [1 ]
Wood, JL [1 ]
机构
[1] Yale Univ, Dept Chem, Sterling Chem Lab, New Haven, CT 06520 USA
关键词
alkaloids; natural products; samarium; total synthesis;
D O I
10.1002/anie.200353282
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The complete carbon skeleton of welwitindolinone A isonitrile has been prepared by using a [2+2] cycloaddition to establish the bicyclo[4.2.0]octane core and a Sml2-mediated intramolecular reductive cyclization between an enone and an aryl isocyanate to stereoselectively install the spiro-oxindole (see scheme; DBU = 1,8-diazabicyclo[5.4.0]undec-7-ene).
引用
收藏
页码:1270 / 1272
页数:3
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