An improved route to (+)-tedanolide and analysis of its subtle effects controlling conformation and biological behaviour.

An improved route to (+)-tedanolide and analysis of its subtle effects controlling conformation and biological behaviour.
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( )-泰那内酯的改进途径及其控制构象和生物行为的微妙作用分析

DOI:
10.1002/chem.201103038
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发表时间:
2012
期刊:
影响因子:
--
通讯作者:
Kalesse
Kalesse
中科院分区:
--
文献类型:
--
作者:
Ehrlich;Eggert;Muthukumar;Kalesse

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通过双酮的醛醇偶联,改进了抗肿瘤化合物(+)‐tedanolide的合成。这种修饰缩短了最后的合成步骤,并提供了快速获得这种生物学上重要的天然产物的途径。此外,它作为一个探针,以揭示阻碍或使其成功合成的构象效应。通过这种方法获得去环氧环氧丹丹内酯,其生物学特性令人惊讶地揭示了其作用模式,类似于白蜡木内酯而不是脱氧丹丹内酯。
The improved synthesis of the antitumor compound (+)‐tedanolide is described through an aldol coupling of bis‐ketone7. This modification shortens the synthetic steps in the endgame and provides rapid access to this biologically important natural product. Additionally, it serves as a probe in order to unravel the conformational effects that impede or enable its successful synthesis. Having this way access to des‐epoxy‐tedanolide, its biological characterization surprisingly unravelled the mode of action to resemble candidaspongiolide rather than deoxytedanolide.
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