Total Synthesis of Aristogin C in Aqueous Systems

Hong-yun, Gao; Ha, Cong-Tu

doi:10.1080/00397910600941125

Cited by 8 publications

(6 citation statements)

References 8 publications

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“…Methyl 3-Bromo-4-methoxybenzoate (2a). 14 Methyl 2-Bromo-5-methoxybenzoate (2b). 15 According to the general procedure, the reaction of 1b (0.035 mL, 0.24 mmol) with PhSTMS (0.023 mL, 0.12 mmol) and NBS (128 mg, 0.72 mmol) in CH 3 CN (1.2 mL) gave 2b (53.9 mg, 92%) after purification by SiO 2 column chromatography (n-Hex/AcOEt = 10/1).…”

Section: The Journal Of Organic Chemistrymentioning

confidence: 99%

Aromatic Halogenation Using N-Halosuccinimide and PhSSiMe₃ or PhSSPh

et al. 2019

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We developed a mild aromatic halogenation reaction using a combination of N-halosuccinimide and PhSSiMe3 or PhSSPh. Less reactive aromatic compounds, such as methyl 4-methoxybenzoate, were brominated with PhSSiMe3 or PhSSPh and N-bromosuccinimide in high yields. No reaction was observed in the absence of PhSSiMe3 or PhSSPh. This method is also applicable to chlorination reactions using N-chlorosuccinimide and PhSSPh.

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Section: The Journal Of Organic Chemistrymentioning

confidence: 99%

Aromatic Halogenation Using N-Halosuccinimide and PhSSiMe₃ or PhSSPh

et al. 2019

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“…Diaryl ether-containing structures have been isolated from lichens (e.g., depsidones), sponges (e.g., bastadines), trees (e.g., combretastatines), mosses (e.g., riccardin B), and several microorganisms (e.g., piperazinomycin) . The structural variety of the isolated diaryl ethers is huge; there are important compounds, such as depsidones or aristogines, containing just two aryl components, and there are complex natural products, vancomycin for example, containing several diaryl ether moieties.…”

Section: Introductionmentioning

confidence: 99%

Diaryl Ether and Diaryl Thioether Syntheses on Solid Supports via Copper (I)-Mediated Coupling

Jung

Bräse

2008

J. Comb. Chem.

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An efficient method to synthesize diaryl ethers and thioethers on solid supports is described. Starting from immobilized phenols or arylhalides, coupling with an access of aryliodides/arylbromides or phenolic/thiophenolic substrates in solution was successful in the presence of CuCl and Cs(2)CO(3) as base. Coupling conditions known from solution-phase syntheses of diaryl ethers have been effectively modified and adapted to solid-phase synthesis. Optimized conditions enabled the coupling of sterically hindered and/or electronically deactivated aryl moieties. After coupling, a newly developed diversity-generating linker based on cinnamic acid allowed the diaryl ethers to be cleaved from the resin either via saponification/transesterification or via ozonolysis. Latter offers the possibility of generating several additional compounds by simple variation of the cleavage conditions. The target substances were generally isolated in good to excellent yields and high purities.

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“…The synthesis of Hernandial (5) was performed on resin 21b through coupling with 2bromo-4,5-dimethoxybenzaldehyde under conditions pre-viously described by our group (Scheme 4). [76] The chosen linkage via a cinnamic ester yields resin-bound Hernandial precursor 25, which can be cleaved from the solid support by ozonolysis in 20 s. Syntheses of Aristogins A-F. Aristogins A, B, C, and E have been synthesized in liquid phase, [82][83][84] but to the best of our knowledge there is no synthetic protocol for the syntheses of Aristogins D and F, neither referring to liquid nor to solid-phase syntheses.…”

Section: Resultsmentioning

confidence: 99%

“…Aristogins A, B, C, and E have been synthesized in liquid phase, [82][83][84] but to the best of our knowledge there is no synthetic protocol for the syntheses of Aristogins D and F, neither referring to liquid nor to solid-phase syntheses.…”

Section: Syntheses Of Aristogins A-fmentioning

confidence: 98%

Synthesis of Natural Products on Solid Phases via Copper‐Mediated Coupling: Synthesis of the Aristogin Family, Spiraformin A, and Hernandial

Jung

Bräse

2009

Eur J Org Chem

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The formation of natural products on solid phases via diaryl ether coupling is presented herein. Starting with either commercially‐available or easily‐producible benzoic, cinnamic, or propionic acids, all immobilized on Merrifield resin via a pentane linker, copper‐mediated couplings yielded solid phase diaryl ethers in good yields. Both, phenol and resins containing aryl halides were used for these Ullmann‐type couplings to generate resin‐bound natural product derivatives. Through cleavage from the resin, eight naturally occurring substances isolated from Aristolochia elegans, Hernandia nymphaeifolia, Spiraea formosana, and Kandelia candel were prepared. To the best of our knowledge, four of these compounds, namely Aristogin D and F as well as Spiraformin A and compound 12 have never previously been synthesized. Gaining access to these natural products on solid supports, demonstrated the utility of diaryl ether formation for the development of combinatorial syntheses. Our approach to diaryl ethers on solid support offers the possibility of synthesizing libraries of natural product derivatives via combinatorial syntheses. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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Total Synthesis of Aristogin C in Aqueous Systems

Cited by 8 publications

References 8 publications

Aromatic Halogenation Using N-Halosuccinimide and PhSSiMe₃ or PhSSPh

Aromatic Halogenation Using N-Halosuccinimide and PhSSiMe₃ or PhSSPh

Diaryl Ether and Diaryl Thioether Syntheses on Solid Supports via Copper (I)-Mediated Coupling

Synthesis of Natural Products on Solid Phases via Copper‐Mediated Coupling: Synthesis of the Aristogin Family, Spiraformin A, and Hernandial

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Total Synthesis of Aristogin C in Aqueous Systems

Cited by 8 publications

References 8 publications

Aromatic Halogenation Using N-Halosuccinimide and PhSSiMe3 or PhSSPh

Aromatic Halogenation Using N-Halosuccinimide and PhSSiMe3 or PhSSPh

Diaryl Ether and Diaryl Thioether Syntheses on Solid Supports via Copper (I)-Mediated Coupling

Synthesis of Natural Products on Solid Phases via Copper‐Mediated Coupling: Synthesis of the Aristogin Family, Spiraformin A, and Hernandial

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Product

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Aromatic Halogenation Using N-Halosuccinimide and PhSSiMe₃ or PhSSPh

Aromatic Halogenation Using N-Halosuccinimide and PhSSiMe₃ or PhSSPh