环氧金霉素 FL-120B'的不对称全合成。
Asymmetric total synthesis of the epoxykinamycin FL-120 B'.
机构信息
Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, MA 02215, USA.
出版信息
Angew Chem Int Ed Engl. 2011 Oct 4;50(41):9722-6. doi: 10.1002/anie.201104504. Epub 2011 Aug 30.
Abstract
[Image: see text] An asymmetric total synthesis of the epoxykinamycin FL-120B’ is reported. The synthesis establishes a route to epoxide-containing diazobenzofluorenes which could potentially serve as monomers to the dimeric lomaiviticins. Key steps include Sharpless asymmetric epoxidation, Stille coupling, and intramolecular Friedel-Crafts acylation of atropisomeric carboxylic acids at elevated temperatures to construct the FL-120B’ core structure.
摘要
[图片：见正文] 本文报道了环氧金霉素 FL-120B' 的不对称全合成。该合成方法建立了一种含环氧基二氮杂苯并菲的合成路线，这些化合物可能作为二聚洛马维丁的单体。关键步骤包括 Sharpless 不对称环氧化、Stille 偶联以及在高温下对非对映异构体羧酸进行分子内 Friedel-Crafts 酰化，以构建 FL-120B' 的核心结构。
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1
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Nat Prod Rep. 2011 Aug;28(8):1426-44. doi: 10.1039/c1np00031d. Epub 2011 May 18.
2
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J Am Chem Soc. 2011 May 18;133(19):7260-3. doi: 10.1021/ja200034b. Epub 2011 Jan 31.
3
Enantioselective synthesis of the lomaiviticin aglycon full carbon skeleton reveals remarkable remote substituent effects during the dimerization event.洛马维菌素苷元全碳骨架的对映选择性合成揭示了二聚化过程中显著的远程取代基效应。
Chemistry. 2010 Nov 22;16(44):13058-62. doi: 10.1002/chem.201002157.
4
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Chem Rev. 2011 Feb 9;111(2):563-639. doi: 10.1021/cr100155e. Epub 2010 Oct 12.
5
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J Am Chem Soc. 2010 Mar 3;132(8):2540-1. doi: 10.1021/ja910769j.
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