Efficient synthesis and resolution of pyrrolizidines

被引:44
作者
de Figueiredo, Renata Marcia
Froehlich, Roland
Christmann, Mathias
机构
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
[2] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany
关键词
antitumor agents; chiral resolution; lactonization; natural products; organocatalysis;
D O I
10.1002/anie.200605035
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In only two steps the commercially available maleimide 1 is converted into the key pyrrolizidine carboxylic acid unit (2) of the telomerase inhibitor UCS1025A. A kinetic resolution through an enantioselective oxa-Michael lactonization and trituration of the resulting scalemic mixture allow for a virtually quantitative separation of a racemate into the enantiomers. (Chemical Equation Presented). © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:2883 / 2886
页数:4
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