A total synthesis of verbenachalcone, a bioactive diaryl ether from Verbena littoralis

Tanabe, Takamasa; Doi, Fuminao; Ogamino, Takahisa; Nishiyama, Shigeru

doi:10.1016/j.tetlet.2004.02.154

Cited by 26 publications

(10 citation statements)

References 10 publications

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“…As far as we are aware, rhuschalcone VI (1) is the first and unique example of a natural dimer in which two chalcones are linked by a C-C bond; and no group has reported the total synthesis of C-C AB bichalcones. It is remarkable that whereas (a) the total synthesis of the bi-aryl ether-type bichalcones (rhuschalcones and verbenachalcone) have been reported, 1,3,4 by employing a novel application of the Ullmann synthesis and through anodic oxidation, respectively, and (b) a 0968-0896/$ -see front matter Ó 2010 Elsevier Ltd. All rights reserved. doi:10.1016/j.bmc.2010.02.055 number of flavonoids have been employed in Suzuki reactions, 5 the use of chalcones and the synthesis of any bi-aryl type rhus bichalcones has not yet been reported.…”

Section: Introductionmentioning

confidence: 99%

Total synthesis, antiprotozoal and cytotoxicity activities of rhuschalcone VI and analogs

Mihigo

Mammo

Bezabih

et al. 2010

Bioorganic & Medicinal Chemistry

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Section: Introductionmentioning

confidence: 99%

Total synthesis, antiprotozoal and cytotoxicity activities of rhuschalcone VI and analogs

Mihigo

Mammo

Bezabih

et al. 2010

Bioorganic & Medicinal Chemistry

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“…Nishiyama and colleagues have successfully reported the electrochemical oxidation of the halogenated phenol‐derivative 23 in methanol to give dienone−arylether 24 followed by its reduction with zinc powder to obtain the corresponding diarylether 25 [39–42] …”

Section: Redox‐combined Synthesismentioning

confidence: 99%

Electrosynthesis in Laminar Flow Using a Flow Microreactor

Shida

Nakamura

Atobe

2021

The Chemical Record

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Electrosynthesis and microflow synthesis have become essential tools in their own rights in modern organic synthesis. In this personal account, we summarize our works on the integrated use of these techniques, i. e., electrosynthesis in a flow microreactor. Our group has developed an electrochemical microflow system composed of a pair of electrodes that face each other to form a micrometer‐scale gap for the flow path, through which solution passes in laminar flow. By the aid of laminar flow, unprecedented chemo‐ and electrochemical selectivity has been observed, which is not achievable with conventional batch‐type electrochemical cells. In addition, we showcase various unique electrochemical systems and reactions achieved with the flow microreactor, including self‐supported electrolysis, efficient paired electrolysis, in situ generation of active species and its flash use, the spaciotemporal control of electropolymerization, and combinatorial screening of the reaction conditions.

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“…Subsequent cathodic reduction and saponification provided intermediate 103 which, upon condensation with dimethoxytyramine (104) followed by Bischler-Napieralski reaction 163 and hydrogenation, provided O-methylthalibrine (105). The same electrochemical technique for the dimerization of phenols into diaryl ethers was utilized in the total synthesis of verbenachalcone 164 and isodityrosine, 165 a natural product which also represents an important substructure in biologically relevant cyclic peptides.…”

Section: Miscellaneous Transformationsmentioning

confidence: 99%

Anodic Oxidation as an Enabling Tool for the Synthesis of Natural Products

Geske

Sato²,

Opatz³

2020

Synthesis

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Electrochemistry provides a valuable toolbox for organic synthesis and offers an appealing, environmentally benign alternative to the use of stoichiometric quantities of chemical oxidants or reductants. Its potential to control current efficiency along with providing alternative reaction conditions in a classical sense makes electrochemistry a suitable method for large-scale industrial transformations as well as for laboratory applications in the synthesis of complex molecular architectures. Even though research in this field has intensified over the recent decades, many synthetic chemists still hesitate to add electroorganic reactions to their standard repertoire, and hence, the full potential of preparative organic electrochemistry has not yet been unleashed. This short review highlights the versatility of anodic transformations by summarizing their application in natural product synthesis.1 Introduction2 Shono-Type Oxidation3 C–N/N–N Bond Formation4 Aryl–Alkene/Aryl–Aryl Coupling5 Cycloadditions Triggered by Oxidation of Electron-Rich Arenes6 Spirocycles7 Miscellaneous Transformations8 Future Prospects

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A total synthesis of verbenachalcone, a bioactive diaryl ether from Verbena littoralis

Cited by 26 publications

References 10 publications

Total synthesis, antiprotozoal and cytotoxicity activities of rhuschalcone VI and analogs

Total synthesis, antiprotozoal and cytotoxicity activities of rhuschalcone VI and analogs

Electrosynthesis in Laminar Flow Using a Flow Microreactor

Anodic Oxidation as an Enabling Tool for the Synthesis of Natural Products

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