(+)-白黄精A和B的简洁全合成
Concise Total Synthesis of (+)-Luteoalbusins A and B.
作者信息
Adams Timothy C, Payette Joshua N, Cheah Jaime H, Movassaghi Mohammad
机构信息
Department of Chemistry, Massachusetts Institute of Technology , 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States.
The Koch Institute for Integrative Cancer Research, Massachusetts Institute of Technology , 500 Main Street, Cambridge, Massachusetts 02139, United States.
出版信息
Org Lett. 2015 Sep 4;17(17):4268-71. doi: 10.1021/acs.orglett.5b02059. Epub 2015 Aug 25.
Abstract
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 a 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.
摘要
本文描述了（+）-淡黄白蛋白A和B的首次全合成。我们合成过程中高度区域和非对映选择性的化学转化包括将傅克C3-吲哚加成到环色氨酸衍生的二酮哌嗪上、后期二酮哌嗪二羟基化以及C11-硫化序列，此外还有同类物特异性多硫烷的合成以及环化生成相应的表聚硫代二酮哌嗪。我们还报告了这两种生物碱以及密切相关衍生物对A549、HeLa、HCT116和MCF7人癌细胞系的细胞毒性。
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2
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3
4
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J Am Chem Soc. 2013 Mar 13;135(10):4117-28. doi: 10.1021/ja400315y. Epub 2013 Mar 1.
8
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9
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10
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