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Total synthesis of dissectol A, using an enediolate-based Tsuji-Trost reaction.
Andringa, Ruben L H; Marinus, Nittert; Bunt, Daan V; Haiderer, Elizabeth R; Abramovitch, Robert B; Brown, Christopher D; Rhee, Kyu Y; Witte, Martin D; Minnaard, Adriaan J.
Affiliation
  • Andringa RLH; Stratingh Institute for Chemistry, University of Groningen Nijenborgh 7, 9747 AG Groningen The Netherlands M.D.Witte@rug.nl A.J.Minnaard@rug.nl.
  • Marinus N; Stratingh Institute for Chemistry, University of Groningen Nijenborgh 7, 9747 AG Groningen The Netherlands M.D.Witte@rug.nl A.J.Minnaard@rug.nl.
  • Bunt DV; Stratingh Institute for Chemistry, University of Groningen Nijenborgh 7, 9747 AG Groningen The Netherlands M.D.Witte@rug.nl A.J.Minnaard@rug.nl.
  • Haiderer ER; Department of Microbiology, Genetics and Immunology, Michigan State University East Lansing MI 48824 USA.
  • Abramovitch RB; Department of Microbiology, Genetics and Immunology, Michigan State University East Lansing MI 48824 USA.
  • Brown CD; Weill Cornell Medicine, Division of Infectious Diseases 1315 York Avenue, Stitch Building New York NY10021 USA.
  • Rhee KY; Weill Cornell Medicine, Division of Infectious Diseases 1315 York Avenue, Stitch Building New York NY10021 USA.
  • Witte MD; Stratingh Institute for Chemistry, University of Groningen Nijenborgh 7, 9747 AG Groningen The Netherlands M.D.Witte@rug.nl A.J.Minnaard@rug.nl.
  • Minnaard AJ; Stratingh Institute for Chemistry, University of Groningen Nijenborgh 7, 9747 AG Groningen The Netherlands M.D.Witte@rug.nl A.J.Minnaard@rug.nl.
Chem Sci ; 15(27): 10541-10546, 2024 Jul 10.
Article in En | MEDLINE | ID: mdl-38994423
ABSTRACT
Dissectol A is a rearranged terpene glycoside isolated from several flowering plants. Starting from glucose, the densely functionalized bicyclic structure has been prepared via site-selective oxidation and an intramolecular allylic alkylation reaction with an enediolate as the nucleophile. Despite earlier reports, dissectol A is not effective at inhibiting DevRS signaling in whole-cell Mycobacterium tuberculosis and does not inhibit growth of the bacterium.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Chem Sci Year: 2024 Document type: Article
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Chem Sci Year: 2024 Document type: Article