A DDQ-mediated ring-opening and aromatization cascade of a tetrahydrocarbazole-fused tetrahydrofuran for the synthesis of olivacine

DİLEK Ö., Patir S., TİLKİ T., Ertürk E.

Tetrahedron Letters, vol.124, 2023 (SCI-Expanded, Scopus) identifier

  • Publication Type: Article / Article
  • Volume: 124
  • Publication Date: 2023
  • Doi Number: 10.1016/j.tetlet.2023.154603
  • Journal Name: Tetrahedron Letters
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Aquatic Science & Fisheries Abstracts (ASFA), BIOSIS, Biotechnology Research Abstracts, CAB Abstracts, Chemical Abstracts Core, Chimica, Veterinary Science Database
  • Keywords: 2,3-Dichloro-5,6-dicyanobenzoquinone, DDQ, DDQ-mediated aromatization, Ellipticine, Natural product, Olivacine, Tetrahydrofuran ring-opening
  • Isparta University of Applied Sciences Affiliated: Yes

Abstract

It is introduced that an N-MOM-tetrahydrocarbazole-fused tetrahydrofuran is a new intermediate for the synthesis of olivacine. Upon treatment with DDQ in a mixture of H2O-THF at 80 °C, it undergoes ring-opening, MOM-removal and aromatization in one pot to yield 1-methyl-carbazole-2-ethanol, an already known precursor for olivacine. Besides, several common transformations, such as α-alklylation of N-MOM-protected tetrahydrocarbazole-1-one with ethyl bromoacetate and reduction of a lactone to tetrahydrofuran with Red-Al, have been made good use.