A Concise Route for the Synthesis of Tetracyclic Meroterpenoids: (±)-Aureol Preparation and Mechanistic Interpretation
| Autor: | Ignacio Rodríguez-García, L. Enriquez, Antonio Rosales Martínez, Emilio Díaz Ojeda, Martín Jaraíz, Laura Pozo Morales |
|---|---|
| Přispěvatelé: | Universidad de Sevilla. Departamento de Ingeniería Química, Universidad de Sevilla. RNM932: Química e Ingeniería Sostenibles |
| Rok vydání: | 2020 |
| Předmět: |
natural products synthesis
Tetracyclic meroterpenoids Stereochemistry Aureol Pharmaceutical Science Natural products - Synthesis Naphthalenes 010402 general chemistry 01 natural sciences Article Interpretation (model theory) Drug Discovery Natural products synthesis lcsh:QH301-705.5 Pharmacology Toxicology and Pharmaceutics (miscellaneous) Molecular Structure 010405 organic chemistry Activator (genetics) Chemistry 0104 chemical sciences Models Chemical lcsh:Biology (General) Yield (chemistry) Productos naturales Sesquiterpenes Química orgánica - Síntesis aureol tetracyclic meroterpenoids |
| Zdroj: | idUS. Depósito de Investigación de la Universidad de Sevilla instname Marine Drugs; Volume 18; Issue 9; Pages: 441 riUAL. Repositorio Institucional de la Universidad de Almería Universidad de Almería idUS: Depósito de Investigación de la Universidad de Sevilla Universidad de Sevilla (US) Marine Drugs, Vol 18, Iss 441, p 441 (2020) Marine Drugs |
| Popis: | Producción Científica A new concise general methodology for the synthesis of different tetracyclic meroterpenoids is reported: (±)-aureol (1), the key intermediate of this general route. The synthesis of (±)-aureol (1) was achieved in seven steps (28% overall yield) from (±)-albicanol. The key steps of this route include a C–C bond-forming reaction between (±)-albicanal and a lithiated arene unit and a rearrangement involving 1,2-hydride and 1,2-methyl shifts promoted by BF3•Et2O as activator and water as initiator. Universidad de Sevilla - (Project 2020/00001014) |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|