Literature DB >> 24514270

Applications of biocatalytic arene ipso,ortho cis-dihydroxylation in synthesis.

Simon E Lewis1.   

Abstract

The dearomatising dihydroxylation of aromatic molecules mediated by arene dioxygenase enzymes can provide cyclohexadiene-diols that are versatile starting materials for organic synthesis. Whereas oxidation of a substituted arene to give its ortho,meta-dihydrodiol has been demonstrated for numerous substrates and dioxygenases, formation of ipso,ortho-dihydrodiols has historically been underutilised in comparison. This feature article presents a chronological account of reported uses of such diols.

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Year:  2014        PMID: 24514270     DOI: 10.1039/c3cc49694e

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  12 in total

1.  Rate-Determining Attack on Substrate Precedes Rieske Cluster Oxidation during Cis-Dihydroxylation by Benzoate Dioxygenase.

Authors:  Brent S Rivard; Melanie S Rogers; Daniel J Marell; Matthew B Neibergall; Sarmistha Chakrabarty; Christopher J Cramer; John D Lipscomb
Journal:  Biochemistry       Date:  2015-07-21       Impact factor: 3.162

2.  Palladium-Catalyzed Dearomative syn-1,4-Carboamination.

Authors:  Mikiko Okumura; Alexander S Shved; David Sarlah
Journal:  J Am Chem Soc       Date:  2017-12-05       Impact factor: 15.419

3.  Organic chemistry: A light touch breaks a strong ring.

Authors:  Martin G Banwell
Journal:  Nat Chem       Date:  2016-09-22       Impact factor: 24.427

4.  Arenophile-Mediated Dearomative Reduction.

Authors:  Mikiko Okumura; Stephanie M Nakamata Huynh; Jola Pospech; David Sarlah
Journal:  Angew Chem Int Ed Engl       Date:  2016-11-23       Impact factor: 15.336

5.  Chemical Equivalent of Arene Monooxygenases: Dearomative Synthesis of Arene Oxides and Oxepines.

Authors:  Zohaib Siddiqi; William C Wertjes; David Sarlah
Journal:  J Am Chem Soc       Date:  2020-05-08       Impact factor: 15.419

6.  Design and Synthesis of C-1 Methoxycarbonyl Derivative of Narciclasine and Its Biological Activity.

Authors:  Lihi Habaz; Korey Bedard; Mitchell Smith; Liqin Du; Alexander Kornienko; Tomas Hudlicky
Journal:  Molecules       Date:  2022-06-14       Impact factor: 4.927

7.  Nickel-Catalyzed Dearomative trans-1,2-Carboamination.

Authors:  Lucas W Hernandez; Ulrich Klöckner; Jola Pospech; Lilian Hauss; David Sarlah
Journal:  J Am Chem Soc       Date:  2018-03-23       Impact factor: 15.419

8.  Synthesis of (+)-Pancratistatins via Catalytic Desymmetrization of Benzene.

Authors:  Lucas W Hernandez; Jola Pospech; Ulrich Klöckner; Tanner W Bingham; David Sarlah
Journal:  J Am Chem Soc       Date:  2017-10-25       Impact factor: 15.419

Review 9.  Benefits of Unconventional Methods in the Total Synthesis of Natural Products.

Authors:  Tomas Hudlicky
Journal:  ACS Omega       Date:  2018-12-14

10.  Chemoenzymatic Total Synthesis of (+)-10-Keto-Oxycodone from Phenethyl Acetate.

Authors:  Mary Ann Endoma-Arias; Helen Dela Paz; Tomas Hudlicky
Journal:  Molecules       Date:  2019-09-25       Impact factor: 4.411

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