A DDQ-mediated ring-opening and aromatization cascade of a tetrahydrocarbazole-fused tetrahydrofuran for the synthesis of olivacine
Tetrahedron Letters, vol.124, 2023 (SCI-Expanded, Scopus)
- 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, EMBASE, Veterinary Science Database
- Keywords: 2,3-Dichloro-5,6-dicyanobenzoquinone, DDQ, DDQ-mediated aromatization, Ellipticine, Natural product, Olivacine, Tetrahydrofuran ring-opening
- Süleyman Demirel University 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.