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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.
  • Deihl ED; Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States.
  • Jesikiewicz LT; Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States.
  • Newman LJ; Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States.
  • Liu P; Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States.
  • Brummond KM; Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States.
Org Lett ; 24(4): 995-999, 2022 02 04.
Article in English | MEDLINE | ID: covidwho-1655437
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.
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Full text: Available Collection: International databases Database: MEDLINE Main subject: Rhodium / Thapsigargin Type of study: Experimental Studies / Randomized controlled trials Language: English Journal: Org Lett Journal subject: Biochemistry Year: 2022 Document Type: Article Affiliation country: Acs.orglett.1c03951

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Full text: Available Collection: International databases Database: MEDLINE Main subject: Rhodium / Thapsigargin Type of study: Experimental Studies / Randomized controlled trials Language: English Journal: Org Lett Journal subject: Biochemistry Year: 2022 Document Type: Article Affiliation country: Acs.orglett.1c03951