Work

Resolution and Absolute Configuration of Fargesin Enantiomers

Year: 2024

Type: article

Abstract: Fargesin is an important bioactive furofuran lignan isolated from different plant species. Despite presenting potent biological activities, its stereochemical characterization has relied mostly on empirical correlations of optical rotation, an approach considered risky that commonly leads to misassignments and error propagation. Additionally, the enantiomeric purity of fargesin isolates used for biological assays has not been previously investigated. Herein, we report the enantioresolution of a scalemic mixture of fargesin isolated from Aristolochia warmingii along with the first unambiguous determination of the absolute configuration of each enantiomer by means of optical rotatory dispersion, as well as electronic and vibrational circular dichroism aided by quantum-chemical calculations.

Source: Chirality

DOI: 10.1002/chir.70003

Authors: Eloá R. Mestriner, Eric Y. Lee, Camila L. Cunha, Victor M. S. Sousa, Isabele R. Nascimento, João M. Batista

Institutions: Universidade Estadual Paulista (Unesp), Universidade Federal de São Paulo

Language: English

Topic: Molecular spectroscopy and chirality

Subfield: Spectroscopy

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Fundação de Amparo à Pesquisa do Estado de São Paulo, Coordenação de Aperfeiçoamento de Pessoal de Nível Superior

Awards: G121811674, Systematizing chiroptical properties of lignans: implications for correct absolute configuration assignments