Oxidative annulation of l-phenylalanine using I₂/DMSO: an easy approach for chemoselective synthesis of 2,3,5-trisubstituted pyridines and 2,5-disubstituted oxazoles

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A facile approach for chemoselective synthesis of 2,3,5-trisubstituted pyridines and 2,5-disubstituted oxazoles from l -phenylalanine aryl methyl ketone using I 2 /DMSO has been developed.

Language: Английский

One‐Pot Gram‐Scale Synthesis of Cynandione A and Detailed Mechanistic Insights into its Regioselectivity

ChemistryOpen, Journal Year: 2025, Volume and Issue: unknown

Published: March 26, 2025

Cynandione A, a natural biaryl product with bis-acetophenone structure isolated from Cynanchi wilfordii Radix, has garnered considerable attention because of its diverse biological activities, including anti-inflammatory, neuroprotective, antioxidant, and adipogenic effects. However, the limited commercial availability cynandione A impedes large-scale evaluations, particularly in vivo studies. Herein, we report one-pot gram-scale synthesis A. The key step this is regioselective conjugate addition acetyl bisphenol to benzoquinone substrate, which been mechanistically explored using density functional theory (DFT) calculations. significant energetic differences at transition states among possible pathways indicate C3 position nucleophile as exclusive site addition. Through careful optimization, affords gram scale high yield. This method presents practical, scalable approach for synthesizing excellent pot economy.

Language: Английский

Advances in Self-Organized Total Synthesis of Natural Products

Chemical Communications, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

In this review, we account for the definition, delimitation, and categorization of self-organized total synthesis then elucidate a comprehensive understanding synthetic strategy based on our intensive explorations.

Language: Английский