A DFT study of the endo-selectivity mechanism of the Diels-Alder reaction in lindenane dimeric sesquiterpene synthesis promoted by pyridines.
Phys Chem Chem Phys
; 25(5): 3772-3779, 2023 Feb 01.
Article
em En
| MEDLINE
| ID: mdl-36644930
ABSTRACT
The lindenane dimeric sesquiterpenoids with versatile biological activities are accessible via biometric synthesis, in which the endo-selective Diels-Alder reaction plays an important role. To explore the endo-selectivity of the Diels-Alder reaction between lindenane sesquiterpenes promoted by pyridines, density functional theory (DFT) calculations were performed to explore the reaction mechanism between pyridines and D-A monomers. The calculations performed on the reaction pathways explain why pyridines can promote endo-selectivity via hydrogen bonding, and the hydrogen bond strength is a key factor driving the Diels-Alder reaction in major biochemical systems. These DFT-level insights will pave the way for designing better promoters for Diels-Alder reactions in biometric synthesis applications.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
Phys Chem Chem Phys
Ano de publicação:
2023
Tipo de documento:
Article