Selectivity of radical formation in the reaction of carbonyl compounds with manganese(III) acetate

Midgley, Gary; Thomas, C. Barry

doi:10.1039/p29870001103

Cited by 10 publications

(3 citation statements)

References 3 publications

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“…Compounds 3 and 4 have been synthesized previously, although most reports are in communication format without experimental details. ,− These accounts all alluded to the fragility of the β-ketoamide functionality; the p K a for enolate formation of andrimid is 6.8 . We prepared anhydride 15 (Scheme ) from commercially available (4 S )-methyl-succinic acid according to Midgley and Thomas and converted this to the benzyl protected succinimide 17 . Indeed, Pohlmann et al had prepared a number of N -alkylated derivatives of moiramide for SAR studies but they did not prepare the benzyl derivative, and it was not clear why they and others used benzyloxy protection for the succinimide nitrogen, which requires two steps for removal.…”

Section: Results and Discussionmentioning

confidence: 99%

Design, Synthesis, and Antibacterial Properties of Dual-Ligand Inhibitors of Acetyl-CoA Carboxylase

et al. 2014

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There is an urgent demand for the development of new antibiotics due to the increase in drug-resistant pathogenic bacteria. A novel target is the multifunctional enzyme acetyl-CoA carboxylase (ACC), which catalyzes the first committed step in fatty acid synthesis and consists of two enzymes: biotin carboxylase and carboxyltransferase. Covalently attaching known inhibitors against these enzymes with saturated hydrocarbon linkers of different lengths generated dual-ligand inhibitors. Kinetic results revealed that the dual-ligands inhibited the ACC complex in the nanomolar range. Microbiology assays showed that the dual-ligand with a 15-carbon linker did not exhibit any antibacterial activity, while the dual-ligand with a 7-carbon linker displayed broad-spectrum antibacterial activity as well as a decreased susceptibility in the development of bacterial resistance. These results suggest that the properties of the linker are vital for antibacterial activity and show how inhibiting two different enzymes with the same compound increases the overall potency while also impeding the development of resistance.

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Section: Results and Discussionmentioning

confidence: 99%

Design, Synthesis, and Antibacterial Properties of Dual-Ligand Inhibitors of Acetyl-CoA Carboxylase

et al. 2014

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“…Reaction of 11 with Mn(OAc) 3 · 2H 2 O generated radical intermediate 18. 19 20 to give the corresponding carbocation 20. Elimination of the trimethylsilyl group in 20 afforded allylated species 21.…”

Section: · 2h 2 O (Scheme 2)mentioning

confidence: 99%

Silicon-controlled Carbon-Carbon Bond Formation and Cyclization between Carbonyl Compounds and Allyltrimethylsilane

Hwu¹,

Shiao²,

Hakimelahi³

1997

Appl. Organometal. Chem.

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The effect of silicon on C–C bond formation between carbonyl compounds and allyltrimethylsilane was investigated. Treatment of 1,3‐diketones, β‐ketoesters or malonates with allyltrimethylsilane in the presence of ceric ammonium nitrate (CAN) in methanol produced the corresponding allylated products. Furthermore, introduction of Mn(OAc)3 · 2H2O into those reactions for replacement or assistance of CAN afforded silicon‐containing cyclopentanes in 51–75% yields. A sequential process involving allylation, free‐radical cyclization and elimination was also developed by use of CAN/Mn (OAc)3 · 2H2O/Cu(OAc)2 · H2O. Accordingly, β‐ketoesters or malonates were allowed to react with allylsilanes in acetic acid to give silicon‐containing cyclopentanes with an exo methylene unit in 52–71% yields. These reactions involved carbocationic and carboradical intermediates, of which formation and chemical activities were controlled by a β‐silyl group. © 1997 by John Wiley & Sons, Ltd.

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“…carbonyl radicals have been shown to add intermolecularly to a variety of electron-rich double bonds including alkenes [6][7][8][9][10][11][12][13] and alkynes. 14 Reactions with enol ethers and enol esters have also been reported 15 and Mellor and coworkers have shown, for example, that this type of reaction can be used to prepare oxaspirolactones or related compounds.…”

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confidence: 99%

Manganese(III) Acetate-mediated Alkylation of 1,3-Dicarbonyls to Form Tricarbonyl Compounds Bearing a Quaternary Carbon Centre

Bar¹,

Parsons²,

Thomas³

2002

Synlett

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Selectivity of radical formation in the reaction of carbonyl compounds with manganese(III) acetate

Cited by 10 publications

References 3 publications

Design, Synthesis, and Antibacterial Properties of Dual-Ligand Inhibitors of Acetyl-CoA Carboxylase

Design, Synthesis, and Antibacterial Properties of Dual-Ligand Inhibitors of Acetyl-CoA Carboxylase

Silicon-controlled Carbon-Carbon Bond Formation and Cyclization between Carbonyl Compounds and Allyltrimethylsilane

Manganese(III) Acetate-mediated Alkylation of 1,3-Dicarbonyls to Form Tricarbonyl Compounds Bearing a Quaternary Carbon Centre

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