Stereoselective Synthesis of Flavonoids: A Brief Overview

• Type: Another Publication in an International Scientific Journal
• Date: 2023

Authors

Pereira, AM (Author) Other; Honorina Cidade (Author) FFUP; Tiritan M.E. (Author) FFUP

Journal

Title: Molecules

Vol. 28 No. 3

Final page: 426

ISSN: 1420-3049

Publisher: MDPI

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Other information

Authenticus ID: P-00X-PG5

DOI: 10.3390/molecules28010426

Abstract (EN): Stereoselective synthesis has been emerging as a resourceful tool because it enables the obtaining of compounds with biological interest and high enantiomeric purity. Flavonoids are natural products with several biological activities. Owing to their biological potential and aiming to achieve enantiomerically pure forms, several methodologies of stereoselective synthesis have been implemented. Those approaches encompass stereoselective chalcone epoxidation, Sharpless asymmetric dihydroxylation, Mitsunobu reaction, and the cycloaddition of 1,4-benzoquinone. Chiral auxiliaries, organo-, organometallic, and biocatalysis, as well as the chiral pool approach were also employed with the goal of obtaining chiral bioactive flavonoids with a high enantiomeric ratio. Additionally, the employment of the Diels-Alder reaction based on the stereodivergent reaction on a racemic mixture strategy or using catalyst complexes to synthesise pure enantiomers of flavonoids was reported. Furthermore, biomimetic pathways displayed another approach as illustrated by the asymmetric coupling of 2-hydroxychalcones driven by visible light. Recently, an asymmetric transfer hydrogen-dynamic kinetic resolution was also applied to synthesise (R,R)-cis-alcohols which, in turn, would be used as building blocks for the stereoselective synthesis of flavonoids.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 33