Synthesis of carbazomycin B by radical arylation of benzene

Crich, David; Rumthao, Sochanchingwung

doi:10.1016/j.tet.2003.12.015

Cited by 59 publications

(26 citation statements)

References 11 publications

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“…An accompanying scope and limitation study revealed that the method operated to provide 2‐nitrobiphenyls in high yields by reacting 1‐iodo‐2‐nitrobenzenes with phenylboronic acids by using Pd(PPh 3 ) 4 as catalyst, with any of the solvent pairs, dimethylformamide/water, acetone/water, methanol/water, or methanol, as reaction medium. To implement the cross‐coupling step for congested 1‐iodo‐2‐nitrobenzene ( 3I ), which we attempted by means of an iodination method disclosed by Crich and collaborators 26. This method afforded 3I but only in a low yield (≈ 30 %).…”

Section: Resultsmentioning

confidence: 99%

A Highly Efficient Pd(PPh₃)₄‐Catalyzed Suzuki Cross‐Coupling Method for the Preparation of 2‐Nitrobiphenyls from 1‐Chloro‐2‐nitrobenzenes and Phenylboronic Acids

2016

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A simple and efficient method for Suzuki cross‐coupling of highly substituted and congested 1‐chloro‐2‐nitrobenzene with phenylboronic acid was developed, investigated, and optimized. The reaction conditions comprises a mixture of MeOH and water (4:1) as the reaction medium, readily available and cheap Pd(PPh3)4 as catalyst, sodium carbonate as base, and microwave heating, which affords a fast reaction rate with good outcomes. The procedure was proven to have high functional group tolerance with phenylboronic acid and for 1‐chloro‐2‐nitrobenzene and thus is a general method for the synthesis of 2‐nitrobiphenyl. The target scaffold, 2‐nitrobiphenyls, was produced in excellent yields with excellent selectivities in all cases.

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Section: Resultsmentioning

confidence: 99%

A Highly Efficient Pd(PPh₃)₄‐Catalyzed Suzuki Cross‐Coupling Method for the Preparation of 2‐Nitrobiphenyls from 1‐Chloro‐2‐nitrobenzenes and Phenylboronic Acids

2016

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“…This recognizes that carbazomycin B has not been previously used in agricultural management. In addition, many synthetic methods of carbazomycin B have been reported ( Crich and Rumthao, 2004 ; Markad and Argade, 2014 ; Singh et al, 2019 ). These methods provide solutions for the industrial production of carbazomycin B.…”

Section: Discussionmentioning

confidence: 99%

Inhibitory Effects of Carbazomycin B Produced by Streptomyces roseoverticillatus 63 Against Xanthomonas oryzae pv. oryzae

et al. 2021

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The present manuscript highlights the potential role of Streptomyces roseoverticillatus 63 (Sr-63) against Xanthomonas oryzae pv. oryzae (Xoo), which is the cause of a disastrous bacterial leaf blight disease with rice worldwide. The disease suppression was achieved under greenhouse conditions. A foliar spray of the fermentation broth of Sr-63 significantly reduced the leaf blight symptoms with rice in Xoo inoculated rice plants. Furthermore, we observed that the carbazomycin B, isolated from the fermentation broth of Sr-63, was demonstrated to have antibacterial activity against Xoo with a minimum inhibitory concentration (MIC) of 8 μg mL–1. The results indicated that carbzomycin B hampered the membrane formation of Xoo, reduced the production of xanthomonadin and extracellular polymeric substance (EPS). The fourier transform infrared spectroscopic (FT-IR) indicated that carbazomycin B changed the components of the cell membrane, then caused a change of the cell surface hydrophobicity of Xoo. Scanning electron microscopy revealed that the Xoo cells treated with carbazomycin B exhibited apparent structural deformation. The results also indicated that carbazomycin B had a negative impact on the metabolism of Xoo, carbazomycin B reduced the activity of malate dehydrogenase (MDH) activity and suppressed the protein expression of Xoo. Overall, our data suggests that Streptomyces roseoverticillatus 63 is a promising biocontrol agent that could be used to combat the bacterial leaf blight diseases of rice.

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“…Iodination of intermediate 4 , step ( e′ ), was initially performed according to a protocol using I 2 in the presence of n ‐butylamine, affording the target iodinated intermediate 6′ , although in low yield (32 %) only. Along with the challenging iodination, we designed and developed a successful Suzuki cross‐coupling reaction to produce 2‐nitro‐1,1′‐biphenyl.…”

Section: Resultsmentioning

confidence: 99%

“…2‐Iodo‐4,6‐dimethoxy‐5‐methyl‐3‐nitrophenol (6′) [1872386–67–8]: A solution of KI (0.332 g, 2 mmol) and iodine (0.295 g, 1.16 mmol) in H 2 O (1 mL) was added dropwise to a aqueous solution of BuNH 2 (20 %, 1.5 mL) and acetic acid 2,4‐dimethoxy‐3‐methyl‐5‐nitrophenyl 4 (0.170 g, 0.67 mmol), for 1–2 min at room temperature. The resulting dark mixture was stirred for 30 min at room temperature, and then poured into CH 2 Cl 2 (50 mL).…”

Section: Methodsmentioning

confidence: 99%

Carbazomycin G: Method Development and Total Synthesis

2018

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A novel total synthesis leading to the carbazole alkaloid carbazomycin G was designed and developed. The outlined synthetic route is composed of twelve synthetic steps including the transformations of the initial simple substrate and intermediates. To realize the designed synthesis, in total six new synthetic methods were developed and implemented to provide the target molecule in an overall yield of 8.3 %.

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Synthesis of carbazomycin B by radical arylation of benzene

Cited by 59 publications

References 11 publications

A Highly Efficient Pd(PPh₃)₄‐Catalyzed Suzuki Cross‐Coupling Method for the Preparation of 2‐Nitrobiphenyls from 1‐Chloro‐2‐nitrobenzenes and Phenylboronic Acids

A Highly Efficient Pd(PPh₃)₄‐Catalyzed Suzuki Cross‐Coupling Method for the Preparation of 2‐Nitrobiphenyls from 1‐Chloro‐2‐nitrobenzenes and Phenylboronic Acids

Inhibitory Effects of Carbazomycin B Produced by Streptomyces roseoverticillatus 63 Against Xanthomonas oryzae pv. oryzae

Carbazomycin G: Method Development and Total Synthesis

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Synthesis of carbazomycin B by radical arylation of benzene

Cited by 59 publications

References 11 publications

A Highly Efficient Pd(PPh3)4‐Catalyzed Suzuki Cross‐Coupling Method for the Preparation of 2‐Nitrobi­phenyls from 1‐Chloro‐2‐nitrobenz­enes and Phenylboronic Acids

A Highly Efficient Pd(PPh3)4‐Catalyzed Suzuki Cross‐Coupling Method for the Preparation of 2‐Nitrobi­phenyls from 1‐Chloro‐2‐nitrobenz­enes and Phenylboronic Acids

Inhibitory Effects of Carbazomycin B Produced by Streptomyces roseoverticillatus 63 Against Xanthomonas oryzae pv. oryzae

Carbazomycin G: Method Development and Total Synthesis

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A Highly Efficient Pd(PPh₃)₄‐Catalyzed Suzuki Cross‐Coupling Method for the Preparation of 2‐Nitrobiphenyls from 1‐Chloro‐2‐nitrobenzenes and Phenylboronic Acids

A Highly Efficient Pd(PPh₃)₄‐Catalyzed Suzuki Cross‐Coupling Method for the Preparation of 2‐Nitrobiphenyls from 1‐Chloro‐2‐nitrobenzenes and Phenylboronic Acids