Concise Total Synthesis of (+)-Luteoalbusins A and B.
Concise Total Synthesis of (+)-Luteoalbusins A and B.
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DOI：
10.1021/acs.orglett.5b02059
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发表时间：
2015-09-04
期刊：
影响因子：
5.2
通讯作者：
Movassaghi M
中科院分区：
文献类型：
--
作者：
Adams TC;Payette JN;Cheah JH;Movassaghi M
首次全合成了（+）-黄白菌素A和B。在我们的合成中高度区域和非对映选择性的化学转化包括Friedel-Crafts C3-吲哚加成到环色氨酸衍生的二酮哌嗪，后期二酮哌嗪二羟基化和C11-硫化序列，以及同源特异性的多硫烷合成和环化到相应的epipolythiodiketopiperazine。我们还报告了这两种生物碱和密切相关的衍生物对A549，HeLa，HCT 116和MCF 7人癌细胞系的细胞毒性。
The first total synthesis of (+)-luteoalbusins A and B is described. Highly regio- and diastereoselective chemical transformations in our syntheses include a Friedel-Crafts C3-indole addition to a cyclotryptophan derived diketopiperazine, a late-stage diketopiperazine dihydroxylation and C11-sulfidation sequence, in addition to congener-specific polysulfane synthesis and cyclization to the corresponding epipolythiodiketopiperazine. We also report the cytoxicity of both alkaloids, and closely related derivatives, against A549, HeLa, HCT116 and MCF7 human cancer cell lines.