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对映选择性全合成普乐迪醇 B:一种强效的剪接体抑制剂。

Enantioselective total synthesis of pladienolide B: a potent spliceosome inhibitor.

机构信息

Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907, USA.

出版信息

Org Lett. 2012 Sep 21;14(18):4730-3. doi: 10.1021/ol301886g. Epub 2012 Sep 6.

Abstract

An enantioselective and convergent total synthesis of pladienolide B (1) is described. Pladienolide B binds to the SF3b complex of a spliceosome and inhibits mRNA splicing activity. The synthesis features an epoxide opening reaction, an asymmetric reduction of a β-keto ester, and a cross metathesis strategy for the side chain synthesis.

摘要

本文描述了普乐地尔 B(1)的对映选择性和收敛性的全合成。普乐地尔 B 与剪接体的 SF3b 复合物结合并抑制 mRNA 剪接活性。该合成方法的特点是环氧化物开环反应、β-酮酯的不对称还原以及侧链合成的交叉复分解策略。

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3
Design, synthesis and initial biological evaluation of a novel pladienolide analog scaffold.
Medchemcomm. 2011 Jan 1;2(9):904-908. doi: 10.1039/C1MD00040C.
4
Synthesis of a pladienolide B analogue with the fully functionalized core structure.
Org Lett. 2011 Aug 5;13(15):3940-3. doi: 10.1021/ol201464m. Epub 2011 Jun 27.
5
Synthesis of the macrocyclic core of (-)-pladienolide B.
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6
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Bioorg Med Chem Lett. 2007 Sep 15;17(18):5159-64. doi: 10.1016/j.bmcl.2007.06.094. Epub 2007 Jul 7.
7
Splicing factor SF3b as a target of the antitumor natural product pladienolide.
Nat Chem Biol. 2007 Sep;3(9):570-5. doi: 10.1038/nchembio.2007.16. Epub 2007 Jul 22.
8
Stereochemistry of pladienolide B.
J Antibiot (Tokyo). 2007 Jun;60(6):364-9. doi: 10.1038/ja.2007.49.
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