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  1. Article: Rh(I)-Catalyzed Allenic Pauson–Khand Reaction to Access the Thapsigargin Core: Influence of Furan and Allenyl Chloroacetate Groups on Enantioselectivity

    Deihl, Eric D. / Jesikiewicz, Luke T. / Newman, Logan J. / Liu, Peng / Brummond, Kay M.

    Organic letters. 2022 Jan. 26, v. 24, no. 4

    2022  

    Abstract: Thapsigargin (Tg) is a potent SERCA pump inhibitor with the potential to treat cancer and COVID-19. We have extended the scope of the asymmetric allenic Pauson–Khand reaction to furan-tethered allene-ynes, a stereoconvergent transformation affording the ... ...

    Abstract Thapsigargin (Tg) is a potent SERCA pump inhibitor with the potential to treat cancer and COVID-19. We have extended the scope of the asymmetric allenic Pauson–Khand reaction to furan-tethered allene-ynes, a stereoconvergent transformation affording the 5,7,5-ring system of Tg in good yields and high enantioselectivity. Computational studies of the oxidative cyclization step show that the furan and chloroacetate groups contribute to this high selectivity.
    Keywords COVID-19 infection ; Ca2-transporting ATPase ; cyclization reactions ; enantioselectivity ; furans
    Language English
    Dates of publication 2022-0126
    Size p. 995-999.
    Publishing place American Chemical Society
    Document type Article
    ISSN 1523-7052
    DOI 10.1021/acs.orglett.1c03951
    Database NAL-Catalogue (AGRICOLA)

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  2. Article ; Online: Rh(I)-Catalyzed Allenic Pauson-Khand Reaction to Access the Thapsigargin Core: Influence of Furan and Allenyl Chloroacetate Groups on Enantioselectivity.

    Deihl, Eric D / Jesikiewicz, Luke T / Newman, Logan J / Liu, Peng / Brummond, Kay M

    Organic letters

    2022  Volume 24, Issue 4, Page(s) 995–999

    Abstract: Thapsigargin (Tg) is a potent SERCA pump inhibitor with the potential to treat cancer and COVID-19. We have extended the scope of the asymmetric allenic Pauson-Khand reaction to furan-tethered allene-ynes, a stereoconvergent transformation affording the ... ...

    Abstract Thapsigargin (Tg) is a potent SERCA pump inhibitor with the potential to treat cancer and COVID-19. We have extended the scope of the asymmetric allenic Pauson-Khand reaction to furan-tethered allene-ynes, a stereoconvergent transformation affording the 5,7,5-ring system of Tg in good yields and high enantioselectivity. Computational studies of the oxidative cyclization step show that the furan and chloroacetate groups contribute to this high selectivity.
    MeSH term(s) COVID-19/drug therapy ; Catalysis ; Chloroacetates/chemistry ; Cyclization ; Furans/chemistry ; Models, Molecular ; Molecular Structure ; Rhodium/chemistry ; Stereoisomerism ; Thapsia/chemistry ; Thapsigargin/analogs & derivatives ; Thapsigargin/chemistry
    Chemical Substances Chloroacetates ; Furans ; Thapsigargin (67526-95-8) ; Rhodium (DMK383DSAC)
    Language English
    Publishing date 2022-01-26
    Publishing country United States
    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.
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/acs.orglett.1c03951
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    This service is chargeable due to the Delivery terms set by subito. Orders including an article and supplementary material will be classified as separate orders. In these cases, fees will be demanded for each order.

    Inter-library loan at ZB MED

    Your chosen title can be delivered directly to ZB MED Cologne location if you are registered as a user at ZB MED Cologne.

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