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  1. Article ; Online: Unanticipated Hydrophobicity Increases of Squalene and Human Skin Oil Films Upon Ozone Exposure.

    Butman, Jana L / Thomson, Regan J / Geiger, Franz M

    The journal of physical chemistry. B

    2022  Volume 126, Issue 45, Page(s) 9417–9423

    Abstract: The C-H and O-H oscillators on the surfaces of thin films of human-derived skin oil and squalene are probed under ambient conditions (300 K, 1 atm total pressure, 40% RH) using second-order vibrational spectroscopy and contact angle goniometry before and ...

    Abstract The C-H and O-H oscillators on the surfaces of thin films of human-derived skin oil and squalene are probed under ambient conditions (300 K, 1 atm total pressure, 40% RH) using second-order vibrational spectroscopy and contact angle goniometry before and after exposure to ppb amounts of ozone. Skin oil and squalene are found to produce different vibrational sum frequency generation spectra in the C-H stretching region, while exposure to ozone results in surface spectra for both materials that is consistent with a loss of C-H oscillators. The measured contact angles show that the hydrophobicity of the films increases following exposure to ozone, consistent with the reduction in C═C···H
    MeSH term(s) Humans ; Squalene/chemistry ; Air Pollution, Indoor/analysis ; Ozone/analysis ; Ozone/chemistry ; Skin/chemistry ; Hydrophobic and Hydrophilic Interactions
    Chemical Substances Squalene (7QWM220FJH) ; Ozone (66H7ZZK23N)
    Language English
    Publishing date 2022-11-04
    Publishing country United States
    Document type Journal Article
    ISSN 1520-5207
    ISSN (online) 1520-5207
    DOI 10.1021/acs.jpcb.2c04849
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article: Recent strategies and tactics for the enantioselective total syntheses of cyclolignan natural products

    Reynolds, Rebekah G. / Nguyen, Huong Quynh Anh / Reddel, Jordan C. T. / Thomson, Regan J.

    Natural product reports. 2022 Mar. 23, v. 39, no. 3

    2022  

    Abstract: Lignan natural products are found in many different plant species and possess numerous useful biological properties, such as anti-inflammatory, antiviral, antioxidant, antibacterial, and antitumor activities. Their utility in both traditional and ... ...

    Abstract Lignan natural products are found in many different plant species and possess numerous useful biological properties, such as anti-inflammatory, antiviral, antioxidant, antibacterial, and antitumor activities. Their utility in both traditional and conventional medicine, coupled with their structural diversity has made them popular synthetic targets over many decades. This review specifically addresses the cyclolignan subclass of the family, which possess both a C8–C8′ and a C2–C7′ linkage between two different phenylpropene units. We present a comprehensive overview of the diverse strategies employed by chemists to achieve enantioselective total syntheses of cyclolignans covering: 2000 to 2021.
    Keywords antioxidants ; enantioselectivity ; lignans ; medicine
    Language English
    Dates of publication 2022-0323
    Size p. 670-702.
    Publishing place The Royal Society of Chemistry
    Document type Article
    ZDB-ID 2002546-4
    ISSN 1460-4752 ; 0265-0568
    ISSN (online) 1460-4752
    ISSN 0265-0568
    DOI 10.1039/d1np00057h
    Database NAL-Catalogue (AGRICOLA)

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  3. Article ; Online: Correction to "A Strategy for the Convergent and Stereoselective Assembly of Polycyclic Molecules".

    Robinson, Emily E / Thomson, Regan J

    Journal of the American Chemical Society

    2018  Volume 140, Issue 22, Page(s) 7043

    Language English
    Publishing date 2018-05-21
    Publishing country United States
    Document type Journal Article ; Published Erratum
    ZDB-ID 3155-0
    ISSN 1520-5126 ; 0002-7863
    ISSN (online) 1520-5126
    ISSN 0002-7863
    DOI 10.1021/jacs.8b04547
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  4. Article ; Online: A Strategy for the Convergent and Stereoselective Assembly of Polycyclic Molecules.

    Robinson, Emily E / Thomson, Regan J

    Journal of the American Chemical Society

    2018  Volume 140, Issue 5, Page(s) 1956–1965

    Abstract: The stereoselective oxidative coupling of cyclic ketones via silyl bis-enol ethers followed by ring-closing metathesis is shown to be a general and powerful reaction sequence for the preparation of diverse polycyclic scaffolds from simple precursors. The ...

    Abstract The stereoselective oxidative coupling of cyclic ketones via silyl bis-enol ethers followed by ring-closing metathesis is shown to be a general and powerful reaction sequence for the preparation of diverse polycyclic scaffolds from simple precursors. The modular strategy successfully constructs substructures prevalent in numerous bioactive natural product families, varying in substitution and carbocyclic composition. Several of the prepared compounds were shown to possess potent cytotoxic activity against a panel of tumor cell lines. The utility of this strategy was further demonstrated by a concise and highly convergent 17-step formal synthesis of the complex antimalarial marine diterpene, (+)-7,20-diisocyanoadociane.
    Language English
    Publishing date 2018--07
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 3155-0
    ISSN 1520-5126 ; 0002-7863
    ISSN (online) 1520-5126
    ISSN 0002-7863
    DOI 10.1021/jacs.7b13234
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  5. Article: Access to α-Pyrazole and α-Triazole Derivatives of Ketones from Oxidative Heteroarylation of Silyl Enolethers

    Dhanju, Sandeep / Caravana, Aidan C / Thomson, Regan J

    Organic letters. 2020 Oct. 01, v. 22, no. 20

    2020  

    Abstract: The synthesis of α-pyrazole and α-triazole derivatives of ketones by the ceric ammonium nitrate-mediated oxidative coupling of enolsilanes with heteroarenes is reported. The reaction proceeds under mild reaction conditions to provide a diversity of ... ...

    Abstract The synthesis of α-pyrazole and α-triazole derivatives of ketones by the ceric ammonium nitrate-mediated oxidative coupling of enolsilanes with heteroarenes is reported. The reaction proceeds under mild reaction conditions to provide a diversity of products, including sterically hindered fully substituted derivatives.
    Keywords ammonium ; couplings ; ketones
    Language English
    Dates of publication 2020-1001
    Size p. 8055-8058.
    Publishing place American Chemical Society
    Document type Article
    Note NALT-AP-4-rerunAP2-fuzzy
    ISSN 1523-7052
    DOI 10.1021/acs.orglett.0c03005
    Database NAL-Catalogue (AGRICOLA)

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  6. Article ; Online: Access to α-Pyrazole and α-Triazole Derivatives of Ketones from Oxidative Heteroarylation of Silyl Enolethers.

    Dhanju, Sandeep / Caravana, Aidan C / Thomson, Regan J

    Organic letters

    2020  Volume 22, Issue 20, Page(s) 8055–8058

    Abstract: The synthesis of α-pyrazole and α-triazole derivatives of ketones by the ceric ammonium nitrate-mediated oxidative coupling of enolsilanes with heteroarenes is reported. The reaction proceeds under mild reaction conditions to provide a diversity of ... ...

    Abstract The synthesis of α-pyrazole and α-triazole derivatives of ketones by the ceric ammonium nitrate-mediated oxidative coupling of enolsilanes with heteroarenes is reported. The reaction proceeds under mild reaction conditions to provide a diversity of products, including sterically hindered fully substituted derivatives.
    MeSH term(s) Cerium/chemistry ; Ketones/chemical synthesis ; Ketones/chemistry ; Molecular Structure ; Oxidation-Reduction ; Pyrazoles/chemical synthesis ; Triazoles/chemical synthesis
    Chemical Substances Ketones ; Pyrazoles ; Triazoles ; Cerium (30K4522N6T) ; pyrazole (3QD5KJZ7ZJ) ; ceric ammonium nitrate (U99S55ED6B)
    Language English
    Publishing date 2020-10-01
    Publishing country United States
    Document type Journal Article ; Research Support, N.I.H., Extramural
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/acs.orglett.0c03005
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  7. Article ; Online: Molecular Chirality and Cloud Activation Potentials of Dimeric α-Pinene Oxidation Products.

    Bellcross, Aleia / Bé, Ariana Gray / Geiger, Franz M / Thomson, Regan J

    Journal of the American Chemical Society

    2021  Volume 143, Issue 40, Page(s) 16653–16662

    Abstract: The surface activity of ten atmospherically relevant α-pinene-derived dimers having varying terminal functional groups and backbone stereochemistry is reported. We find ∼10% differences in surface activity between diastereomers of the same dimer, ... ...

    Abstract The surface activity of ten atmospherically relevant α-pinene-derived dimers having varying terminal functional groups and backbone stereochemistry is reported. We find ∼10% differences in surface activity between diastereomers of the same dimer, demonstrating that surface activity depends upon backbone stereochemistry. Octanol-water (
    Language English
    Publishing date 2021-10-04
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't ; Research Support, U.S. Gov't, Non-P.H.S.
    ZDB-ID 3155-0
    ISSN 1520-5126 ; 0002-7863
    ISSN (online) 1520-5126
    ISSN 0002-7863
    DOI 10.1021/jacs.1c07509
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  8. Article ; Online: Recent strategies and tactics for the enantioselective total syntheses of cyclolignan natural products.

    Reynolds, Rebekah G / Nguyen, Huong Quynh Anh / Reddel, Jordan C T / Thomson, Regan J

    Natural product reports

    2022  Volume 39, Issue 3, Page(s) 670–702

    Abstract: Covering: 2000 to 2021Lignan natural products are found in many different plant species and possess numerous useful biological properties, such as anti-inflammatory, antiviral, antioxidant, antibacterial, and antitumor activities. Their utility in both ... ...

    Abstract Covering: 2000 to 2021Lignan natural products are found in many different plant species and possess numerous useful biological properties, such as anti-inflammatory, antiviral, antioxidant, antibacterial, and antitumor activities. Their utility in both traditional and conventional medicine, coupled with their structural diversity has made them popular synthetic targets over many decades. This review specifically addresses the cyclolignan subclass of the family, which possess both a C8-C8' and a C2-C7' linkage between two different phenylpropene units. We present a comprehensive overview of the diverse strategies employed by chemists to achieve enantioselective total syntheses of cyclolignans covering: 2000 to 2021.
    MeSH term(s) Antiviral Agents ; Biological Products/chemistry ; Plants ; Stereoisomerism
    Chemical Substances Antiviral Agents ; Biological Products
    Language English
    Publishing date 2022-03-23
    Publishing country England
    Document type Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't ; Research Support, U.S. Gov't, Non-P.H.S. ; Review
    ZDB-ID 2002546-4
    ISSN 1460-4752 ; 0265-0568
    ISSN (online) 1460-4752
    ISSN 0265-0568
    DOI 10.1039/d1np00057h
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  9. Article ; Online: Organic synthesis in the study of terpene-derived oxidation products in the atmosphere.

    Upshur, Mary Alice / Bé, Ariana Gray / Luo, Jingyi / Varelas, Jonathan G / Geiger, Franz M / Thomson, Regan J

    Natural product reports

    2023  Volume 40, Issue 4, Page(s) 890–921

    Abstract: Covering: 1997 up to 2022Volatile biogenic terpenes involved in the formation of secondary organic aerosol (SOA) particles participate in rich atmospheric chemistry that impacts numerous aspects of the earth's complex climate system. Despite the ... ...

    Abstract Covering: 1997 up to 2022Volatile biogenic terpenes involved in the formation of secondary organic aerosol (SOA) particles participate in rich atmospheric chemistry that impacts numerous aspects of the earth's complex climate system. Despite the importance of these species, understanding their fate in the atmosphere and determining their atmospherically-relevant properties has been limited by the availability of authentic standards and probe molecules. Advances in synthetic organic chemistry directly aimed at answering these questions have, however, led to exciting discoveries at the interface of chemistry and atmospheric science. Herein we provide a review of the literature regarding the synthesis of commercially unavailable authentic standards used to analyze the composition, properties, and mechanisms of SOA particles in the atmosphere.
    MeSH term(s) Terpenes/chemistry ; Atmosphere/chemistry ; Climate ; Oxidation-Reduction ; Chemistry Techniques, Synthetic
    Chemical Substances Terpenes
    Language English
    Publishing date 2023-04-26
    Publishing country England
    Document type Journal Article ; Review ; Research Support, U.S. Gov't, Non-P.H.S.
    ZDB-ID 2002546-4
    ISSN 1460-4752 ; 0265-0568
    ISSN (online) 1460-4752
    ISSN 0265-0568
    DOI 10.1039/d2np00064d
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  10. Article ; Online: Correction: Ring-opening yields and auto-oxidation rates of the resulting peroxy radicals from OH-oxidation of α-pinene and β-pinene.

    Lee, Ben H / Iyer, Siddharth / Kurtén, Theo / Varelas, Jonathan G / Luo, Jingyi / Thomson, Regan J / Thornton, Joel A

    Environmental science: atmospheres

    2023  Volume 3, Issue 12, Page(s) 1847

    Abstract: This corrects the article DOI: 10.1039/D2EA00133K.]. ...

    Abstract [This corrects the article DOI: 10.1039/D2EA00133K.].
    Language English
    Publishing date 2023-11-27
    Publishing country England
    Document type Published Erratum
    ISSN 2634-3606
    ISSN (online) 2634-3606
    DOI 10.1039/d3ea90045b
    Database MEDical Literature Analysis and Retrieval System OnLINE

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