Literature DB >> 19132926

An approach to 3,6-disubstituted 2,5-dioxybenzoquinones via two sequential Suzuki couplings. three-step synthesis of leucomelone.

Xianwen Gan1, Wei Jiang, Wei Wang, Lihong Hu.   

Abstract

Two sequential Suzuki coupling reactions have been developed for efficient synthesis of synthetically and biologically important 3,6-disubstituted 2,5-dioxybenzoquinone architectures in a highly chemoselective controlled manner. The method serves as a key step in the total synthesis of leucomelone in three steps and in 61% overall yield.

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Year:  2009        PMID: 19132926     DOI: 10.1021/ol802645f

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  11 in total

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2.  Practical C-H functionalization of quinones with boronic acids.

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3.  Late-Stage C-H Alkylation of Heterocycles and 1,4-Quinones via Oxidative Homolysis of 1,4-Dihydropyridines.

Authors:  Álvaro Gutiérrez-Bonet; Camille Remeur; Jennifer K Matsui; Gary A Molander
Journal:  J Am Chem Soc       Date:  2017-08-23       Impact factor: 15.419

4.  Structure and Function of a Dual Reductase-Dehydratase Enzyme System Involved in p-Terphenyl Biosynthesis.

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Journal:  ACS Chem Biol       Date:  2021-11-11       Impact factor: 5.100

Review 5.  Sequential and iterative Pd-catalyzed cross-coupling reactions in organic synthesis.

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6.  Iron catalyzed C-C dehydrogenative coupling reaction: synthesis of arylquinones from quinones/hydroquinones.

Authors:  Yu Dong; Chun Xie; Jia Chen; Ai Shen; Qi-Qi Luo; Bing He; Zhi-Fan Wang; Bo Chang; Fan Yang; Zhi-Chuan Shi
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7.  Palladium-catalyzed direct C-H functionalization of benzoquinone.

Authors:  Sarah E Walker; James A Jordan-Hore; David G Johnson; Stuart A Macgregor; Ai-Lan Lee
Journal:  Angew Chem Int Ed Engl       Date:  2014-10-10       Impact factor: 15.336

8.  2,5-Di-bromo-3,6-dimeth-oxycyclo-hexa-2,5-diene-1,4-dione.

Authors:  Ersin Orhan; Amine Garci; Bruno Therrien
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-05-24

9.  A focused library synthesis and cytotoxicity of quinones derived from the natural product bolinaquinone.

Authors:  Azadeh Ghods; Jayne Gilbert; Jennifer R Baker; Cecilia C Russell; Jennette A Sakoff; Adam McCluskey
Journal:  R Soc Open Sci       Date:  2018-04-04       Impact factor: 2.963

10.  Regioselective Oxidative Arylation of Fluorophenols.

Authors:  Congjun Yu; Frederic W Patureau
Journal:  Angew Chem Int Ed Engl       Date:  2019-10-31       Impact factor: 15.336

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