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Synthesis of (-)-Dihydroraputindole D by Enantioselective Benzoylation of a 1,3-Diol Intermediate.

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  • المؤلفون: Fresia M;Fresia M; Kock M; Kock M; Lindel T; Lindel T
  • المصدر:
    Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2020 Oct 06; Vol. 26 (56), pp. 12733-12737. Date of Electronic Publication: 2020 Sep 16.
  • نوع النشر :
    Journal Article
  • اللغة:
    English
  • معلومة اضافية
    • المصدر:
      Publisher: Wiley-VCH Country of Publication: Germany NLM ID: 9513783 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1521-3765 (Electronic) Linking ISSN: 09476539 NLM ISO Abbreviation: Chemistry Subsets: PubMed not MEDLINE; MEDLINE
    • بيانات النشر:
      Original Publication: Weinheim, Germany : Wiley-VCH
    • نبذة مختصرة :
      The enantioselective synthesis of (-)-dihydroraputindole D is reported. The key step is the desymmetrizing benzoylation of a prochiral 1,3-diol employing Trost's ProPhenol catalyst system, which has been applied for the first time to a cyclic molecule carrying geminal hydroxymethyl groups. The cyclopenta[f]indoline system was assembled by Au(I)-catalyzed cyclization of an alkynylated indoline precursor. (-)-Dihydroraputindole D was obtained in 17 steps and 8% overall yield starting from dihydroxyacetone. In combination with quantum chemical calculations of the ECD spectra, our synthesis allowed us to determine the absolute configuration (5S,7R) of the natural product (+)-raputindole D from the Rutaceous plant Raputia simulans.
      (© 2020 The Authors. Published by Wiley-VCH GmbH.)
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    • Contributed Indexing:
      Keywords: asymmetric synthesis; desymmetrization; gold catalysis; indole alkaloids; natural products
    • الموضوع:
      Date Created: 20200730 Date Completed: 20201014 Latest Revision: 20201031
    • الموضوع:
      20221213
    • الرقم المعرف:
      PMC7590097
    • الرقم المعرف:
      10.1002/chem.202002579
    • الرقم المعرف:
      32725857