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Article Abstract
A benzene-free synthesis of multisubstituted catechol via an oxidative dearomatic reorganization is reported. This reaction tolerated a wide spectrum of functionalities, which could be applied in the synthesis of an electron-deficient arene-conjugated catechol that is difficult to access via biomimetic oxidative coupling. In addition, a diversification-oriented transformation that leveraged the versatile catechol afforded a series of functionality-rich products.
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Benzene-Free Synthesis of Multisubstituted Catechol via Oxidative Dearomatic Reorganization.
Org Lett
February 2021
Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, P. R. China.
A benzene-free synthesis of multisubstituted catechol via an oxidative dearomatic reorganization is reported. This reaction tolerated a wide spectrum of functionalities, which could be applied in the synthesis of an electron-deficient arene-conjugated catechol that is difficult to access via biomimetic oxidative coupling. In addition, a diversification-oriented transformation that leveraged the versatile catechol afforded a series of functionality-rich products.
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Carbohydr Res
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Center for Materials Characterization, CSIR- National Chemical Laboratory, Pashan Road, Pune, 411008, India. Electronic address:
A method for the preparation of benzene derivatives from myo-inositol, an abundantly available phyto chemical is described. 1,3-Bridged acetals of inososes undergo step-wise elimination leading to the formation of polyoxygenated benzene derivatives. This aromatization reaction proceeds through the intermediacy of a β-alkoxyenone, which could be isolated.
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a Department of Bioscience , Tokyo University of Agriculture, Tokyo , Japan.
Owing to their photosynthetic capabilities, there is increasing interest in utilizing cyanobacteria to convert solar energy into biomass. 2-Deoxy-scyllo-inosose (DOI) is a valuable starting material for the benzene-free synthesis of catechol and other benzenoids. DOI synthase (DOIS) is responsible for the formation of DOI from d-glucose-6-phosphate (G6P) in the biosynthesis of 2-deoxystreptamine-containing aminoglycoside antibiotics such as neomycin and butirosin.
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J Biotechnol
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Faculty of Applied Life Sciences, Niigata University of Pharmacy and Applied Life Sciences, Higashijima 265-1, Niitsu, Niigata 956-8603, Japan.
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J Am Chem Soc
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Department of Chemistry, Michigan State University, East Lansing, Michigan 48824, USA.
The toxicity of aromatics frequently limits the yields of their microbial synthesis. For example, the 5% yield of catechol synthesized from glucose by Escherichia coli WN1/pWL1.290A under fermentor-controlled conditions reflects catechol's microbial toxicity.
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