Regioselectivity and stereoselectivity of dioxygenase catalysed cis-dihydroxylation of mono- and tri-cyclic azaarene substrates

Boyd, Derek R.; Sharma, Narain D.; Coen, Gerard P.; Hempenstall, Francis; Ljubez, Vera; Malone, John F.; Allen, Christopher C. R.; Hamilton, John T. G.

doi:10.1039/b810235j

Cited by 30 publications

(43 citation statements)

References 29 publications

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“…This method of synthesising cis-tetrahydrodiols 3g-i provides an attractive alternative to use of the TDO-catalysed cis-dihydroxylation (P. putida UV4) of 2-, 3-and 4-phenylpyridines to form the corresponding cis-dihydrodiols 1g-i (yield < 5%) and their subsequent partial hydrogenations. Biphenyl dioxygenase (BPDO), present in a mutant strain (B8/36) of Sphingomonas yanoikuyae, [23] gave a better yield (31% to 59%) of the biaryl cis-dihydrodiols 1g-i.…”

Section: Resultsmentioning

confidence: 99%

Cycloalkenyl Halide Substitution Reactions of Enantiopure Arene cis‐Tetrahydrodiols with Boron, Nitrogen and Phosphorus Nucleophiles

et al. 2011

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Enantiopure arene cis-tetrahydrodiols of bromobenzene and iodobenzene have been obtained in good yields, from chemoselective hydrogenation (rhodium-graphite) of the corresponding cis-dihydrodiol metabolites. Palladium-catalysed substitution of the halogen, by hydrogen, boron, nitrogen and phosphorus nucleophiles, in the acetonide derivatives, has yielded highly functionalised products for application in synthesis with potential as scaffolds for chiral ligands.

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Section: Resultsmentioning

confidence: 99%

Cycloalkenyl Halide Substitution Reactions of Enantiopure Arene cis‐Tetrahydrodiols with Boron, Nitrogen and Phosphorus Nucleophiles

et al. 2011

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“…NCIB 9816-4 had not been reported to oxidize many isolated ring structures. All known substrates in this ring class, biphenyl, two flavones, and biphenyllike compounds with heteroatoms, are direct-linked ring compounds (11)(12)(13). No bridge-linked isolated ring substrates have been identified previously.…”

Section: Frac Water Ring Compounds Testedmentioning

confidence: 99%

Use of Silica-Encapsulated Pseudomonas sp. Strain NCIB 9816-4 in Biodegradation of Novel Hydrocarbon Ring Structures Found in Hydraulic Fracturing Waters

Aukema

Kasinkas

Aksan

et al. 2014

Appl Environ Microbiol

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The most problematic hydrocarbons in hydraulic fracturing (fracking) wastewaters consist of fused, isolated, bridged, and spiro ring systems, and ring systems have been poorly studied with respect to biodegradation, prompting the testing here of six major ring structural subclasses using a well-characterized bacterium and a silica encapsulation system previously shown to enhance biodegradation. The direct biological oxygenation of spiro ring compounds was demonstrated here. These and other hydrocarbon ring compounds have previously been shown to be present in flow-back waters and waters produced from hydraulic fracturing operations. Pseudomonas sp. strain NCIB 9816-4, containing naphthalene dioxygenase, was selected for its broad substrate specificity, and it was demonstrated here to oxidize fundamental ring structures that are common in shale-derived waters but not previously investigated with this or related enzymes. Pseudomonas sp. NCIB 9816-4 was tested here in the presence of a silica encasement, a protocol that has previously been shown to protect bacteria against the extremes of salinity present in fracking wastewaters. These studies demonstrate the degradation of highly hydrophobic compounds by a silica-encapsulated model bacterium, demonstrate what it may not degrade, and contribute to knowledge of the full range of hydrocarbon ring compounds that can be oxidized using Pseudomonas sp. NCIB 9816-4.

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“…[10] Only engineered enzymes can produce such compounds; however, their synthetic application has not been explored. [11] …”

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confidence: 99%

Total Synthesis of Lycoricidine and Narciclasine by Chemical Dearomatization of Bromobenzene

2017

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The total synthesis of lycoricidine and narciclasine is enabled by an arenophile-mediated dearomative dihydroxylation of bromobenzene. Subsequent transpositive Suzuki coupling and cycloreversion deliver a key biaryl dihydrodiol intermediate, which is rapidly converted into lycoricidine through site-selective syn-1,4-hydroxyamination and deprotection. The total synthesis of narciclasine is accomplished by the late-stage, amide-directed C–H hydroxylation of a lycoricidine intermediate. Moreover, the general applicability of this strategy to access dihydroxylated biphenyls is demonstrated with several examples.

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Regioselectivity and stereoselectivity of dioxygenase catalysed cis-dihydroxylation of mono- and tri-cyclic azaarene substrates

Cited by 30 publications

References 29 publications

Cycloalkenyl Halide Substitution Reactions of Enantiopure Arene cis‐Tetrahydrodiols with Boron, Nitrogen and Phosphorus Nucleophiles

Cycloalkenyl Halide Substitution Reactions of Enantiopure Arene cis‐Tetrahydrodiols with Boron, Nitrogen and Phosphorus Nucleophiles

Use of Silica-Encapsulated Pseudomonas sp. Strain NCIB 9816-4 in Biodegradation of Novel Hydrocarbon Ring Structures Found in Hydraulic Fracturing Waters

Total Synthesis of Lycoricidine and Narciclasine by Chemical Dearomatization of Bromobenzene

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