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Arene Oxide

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Derek R Boyd – 1st expert on this subject based on the ideXlab platform

  • Synthesis of benzo[g]chrysene, benzo[g]chrysene 9,10-Oxide and benzo[g]chrysene 1,2 : 9,10-diOxide
    Journal of The Chemical Society-perkin Transactions 1, 2016
    Co-Authors: Shiv K. Agarwal, Derek R Boyd, W. Brian Jennings

    Abstract:

    Benzo[g]chrysene has been synthesised and used in the preparation of the K-region Arene Oxide, benzo[g]chrysene 9,10-Oxide. Attempts to synthesise the fjord region Arene Oxide, benzo[g]chrysene 1,2-Oxide, were unsuccessful but a fjord region diArene Oxide, benzo[g]chrysene 1,2 : 9,10-diOxide has been obtained.

  • Synthesis and thermal racemization of the predominant Arene Oxide metabolite of chrysene, (+)-(3S,4R)-chrysene 3,4-Oxide
    Journal of The Chemical Society-perkin Transactions 1, 2016
    Co-Authors: Derek R Boyd, Michael G. Burnett, Ruth M. E. Greene

    Abstract:

    (–)-trans-4-Bromo-3-hydroxy-1,2,3,4-tetrahydrochrysene has been obtained from the chromatographic separation and cleavage of the corresponding menthyloxyacetyl (MOA) diastereoisomer. The (–)-enantiomer of this bromohydrin has been assigned (3R,4R)absolute stereochemistry and used in the synthesis of (+)-(3S,4R)-chrysene 3,4-Oxide. Thermal racemization studies on this Arene Oxide gave a barrier to racemization (Ea) of 25.15 kcal mol–1 and an activation entropy (ΔS‡) of 0.7 cal mol–1 K–1, in accord with PMO predictions.

  • biphenyl dioxygenase catalysed cis dihydroxylation of tricyclic azaArenes chemoenzymatic synthesis of Arene Oxide metabolites and furoquinoline alkaloids
    RSC Advances, 2013
    Co-Authors: Derek R Boyd, Narain D Sharma, Jonathan G Carroll, Pui L Loke, Colin Odowd, Christopher C R Allen

    Abstract:

    Biotransformation of acridine, dictamnine and 4-chlorofuro[2,3-b]quinolone, using whole cells of Sphingomonas yanoikuyae B8/36, yielded five enantiopure cyclic cis-dihydrodiols, from biphenyl dioxygenase-catalysed dihydroxylation of the carbocyclic rings. cis-Dihydroxylation of the furan ring in dictamnine and 4-chlorofuro[2,3-b]quinoline, followed by ring opening and reduction, yielded two exocyclic diols. The structures and absolute configurations of metabolites have been determined by spectroscopy and stereochemical correlation methods. Enantiopure Arene Oxide metabolites of acridine and dictamnine have been synthesised, from the corresponding cis-dihydrodiols. The achiral furoquinoline alkaloids robustine, γ-fagarine, haplopine, isohaplopine-3,3′-dimethylallylether and pteleine have been obtained, from either cis-dihydrodiol, catechol or Arene Oxide metabolites of dictamnine.

Ronald G Harvey – 2nd expert on this subject based on the ideXlab platform

  • Arene Oxide synthesis phenanthrene 9 10 Oxide
    Organic Syntheses, 2003
    Co-Authors: Cecilia Cortez, Ronald G Harvey

    Abstract:

    Arene Oxide SYNTHESIS: PHENANTHRENE-9,10-Oxide

    intermediate: trans-9,10-Dihydro-9,10-phenanthrenediol (1)

    product: Phenanthrene-9,10-Oxide (2)

    Keywords:

    elimination, dehydration;
    epOxide formation;
    reduction, CO choh;
    9,10-phenanthrenequinone;
    tetrahydrofuran

  • Organic Syntheses – Arene Oxide Synthesis: Phenanthrene‐9,10‐Oxide
    Organic Syntheses, 2003
    Co-Authors: Cecilia Cortez, Ronald G Harvey

    Abstract:

    Arene Oxide SYNTHESIS: PHENANTHRENE-9,10-Oxide

    intermediate: trans-9,10-Dihydro-9,10-phenanthrenediol (1)

    product: Phenanthrene-9,10-Oxide (2)

    Keywords:

    elimination, dehydration;
    epOxide formation;
    reduction, CO choh;
    9,10-phenanthrenequinone;
    tetrahydrofuran

Narain D Sharma – 3rd expert on this subject based on the ideXlab platform

  • biphenyl dioxygenase catalysed cis dihydroxylation of tricyclic azaArenes chemoenzymatic synthesis of Arene Oxide metabolites and furoquinoline alkaloids
    RSC Advances, 2013
    Co-Authors: Derek R Boyd, Narain D Sharma, Jonathan G Carroll, Pui L Loke, Colin Odowd, Christopher C R Allen

    Abstract:

    Biotransformation of acridine, dictamnine and 4-chlorofuro[2,3-b]quinolone, using whole cells of Sphingomonas yanoikuyae B8/36, yielded five enantiopure cyclic cis-dihydrodiols, from biphenyl dioxygenase-catalysed dihydroxylation of the carbocyclic rings. cis-Dihydroxylation of the furan ring in dictamnine and 4-chlorofuro[2,3-b]quinoline, followed by ring opening and reduction, yielded two exocyclic diols. The structures and absolute configurations of metabolites have been determined by spectroscopy and stereochemical correlation methods. Enantiopure Arene Oxide metabolites of acridine and dictamnine have been synthesised, from the corresponding cis-dihydrodiols. The achiral furoquinoline alkaloids robustine, γ-fagarine, haplopine, isohaplopine-3,3′-dimethylallylether and pteleine have been obtained, from either cis-dihydrodiol, catechol or Arene Oxide metabolites of dictamnine.

  • Chemoenzymatic synthesis of monocyclic Arene Oxides and Arene hydrates from substituted benzene substrates.
    Organic and Biomolecular Chemistry, 2013
    Co-Authors: Derek R Boyd, Narain D Sharma, Vera Ljubez, Peter K. M. Mcgeehin, Paul J. Stevenson, Marine Blain, Christopher C R Allen

    Abstract:

    Enantiopure cis-dihydrodiol bacterial metabolites of substituted benzene substrates were used as precursors, in a chemoenzymatic synthesis of the corresponding benzene Oxides and of a substituted oxepine, via dihydrobenzene Oxide intermediates. A rapid total racemization of the substituted benzene 2,3-Oxides was found to have occurred, via their oxepine valence tautomers, in accord with predictions and theoretical calculations. Reduction of a substituted Arene Oxide to yield a racemic Arene hydrate was observed. Arene hydrates have also been synthesised, in enantiopure form, from the corresponding dihydroArene Oxide or trans-bromoacetate precursors. Biotransformation of one Arene hydrate enantiomer resulted in a toluene-dioxygenase catalysed cis-dihydroxylation to yield a benzene cis-triol metabolite.

  • Enzyme-catalysed synthesis and reactions of benzene Oxide/oxepine derivatives of methyl benzoates
    Organic and Biomolecular Chemistry, 2008
    Co-Authors: Derek R Boyd, Narain D Sharma, John F Malone, John S. Harrison, W. C. Mcroberts, John T. G. Hamilton, David B. Harper

    Abstract:

    A series of twelve benzoate esters was metabolised, by species of the Phellinus genus of wood-rotting fungi, to yield the corresponding benzyl alcohol derivatives and eight salicylates. The isolation of a stable oxepine metabolite, from methyl benzoate, allied to evidence of the migration and retention of a carbomethoxy group (the NIH Shift), during enzyme-catalysed ortho-hydroxylation of alkyl benzoates to form salicylates, is consistent with a mechanism involving an initial Arene epoxidation step. This mechanism was confirmed by the isolation of a remarkably stable, optically active, substituted benzene Oxide metabolite of methyl 2-(trifluoromethyl)benzoate, which slowly converted into the racemic form. The Arene Oxide was found to undergo a cycloaddition reaction with 4-phenyl-1,2,4-triazoline-3,5-dione to yield a crystalline cycloadduct whose structure and racemic nature was established by X-ray crystallography. The metabolite was also found to undergo some novel benzene Oxide reactions, including epoxidation to give an anti-diepOxide, base-catalysed hydrolysis to form a trans-dihydrodiol and acid-catalysed aromatisation to yield a salicylate derivative via the NIH Shift of a carbomethoxy group.