A concise sultone route to highly oxygenated 1,10-seco-eudesmanolides -: Enantioselective total synthesis of the antileukemic sesquiterpene lactones (-)-eriolanin and (-)-eriolangin
A concise sultone route to highly oxygenated 1,10-seco-eudesmanolides -: Enantioselective total synthesis of the antileukemic sesquiterpene lactones (-)-eriolanin and (-)-eriolangin
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DOI：
10.1002/ejoc.200500739
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发表时间：
2006-02-27
影响因子：
2.8
通讯作者：
Metz, P
中科院分区：
文献类型：
--
作者：
Merten, J;Hennig, A;Metz, P
以磺内酯为关键中间体，首次实现了抗白细胞活性的1,10-seco-eudesmanolides (-)-eriolanin (1) 和 (-)-eriolangin (2) 的对映选择性全合成，同时也建立了这些倍半萜内酯迄今为止未知的绝对构型。从 2-溴-1-(2-呋喃基)乙酮开始，需要 24 个步骤来生成共同的基本结构，并在每种情况下需要两个附加步骤来完成天然产物。通过流式细胞术研究1和2对人白血病(HL-60)细胞的细胞周期的影响。 （(c) Wiley-VCH Verlag GmbH & Co. KGaA，69451 Weinheim，德国，2006 年）。
Using a sultone as the key intermediate, the first enantioselective total synthesis of the antileukernic 1,10-seco-eudesmanolides (-)-eriolanin (1) and (-)-eriolangin (2) was achieved, which also established the hitherto unknown absolute configuration of these sesquiterpene lactones. Starting from 2-bromo-1-(2-furyl)ethanone, 24 steps were required to generate the common basic structure and two additional steps in each case for completion of the natural products. The effect of 1 and 2 on the cell cycle of human leukemia (HL-60) cells was investigated by flow cytometry. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006).