Palladium-Catalyzed Synthesis of Pyrayaquinones, Murrayaquinones, and Murrayafoline-B
| Autor: | Sebastian K. Kutz, Arndt W. Schmidt, Hans-Joachim Knölker |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
Annulation
Murraya biology 010405 organic chemistry Chemistry Carbazole Stereochemistry Organic Chemistry chemistry.chemical_element Total synthesis 010402 general chemistry Ring (chemistry) biology.organism_classification 01 natural sciences Catalysis 0104 chemical sciences chemistry.chemical_compound Pyran Frémy's salt Palladium |
| Zdroj: | Synthesis. 49:275-292 |
| ISSN: | 1437-210X 0039-7881 |
| DOI: | 10.1055/s-0036-1588322 |
| Popis: | We describe the total synthesis of murrayafoline-B and seven carbazole-1,4-quinone alkaloids. A palladium(II)-catalyzed oxidative cyclization is used to construct the carbazole skeleton. Pyran annulation and oxidation provide pyrayaquinone-A, -B, and -C. DIBAL-H-promoted reductive ring opening of pyrano[3,2-a]carbazole precursors leads to the prenylated and geranylated carbazole-1,4-quinone alkaloids murrayaquinone-B, -C, -D, and -E and to murrayafoline-B. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|