Recent Advances and Strategies towards Synthesis of Indolyl and Tryptophan‐C‐Glycoside Scaffolds

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(7), P. 1484 - 1508

Published: Feb. 29, 2024

Abstract Recently, C ‐glycosidic bonds have emerged as pivotal elementary units present in many naturally occurring alkaloids well pharmaceutically active molecules. Because of the stability and great utility ‐glycosides, synthetic approaches en route to C−C bond formation gradually become a center attraction carbohydrate chemistry. Towards these researches, ‐glycosylation with heteroaryl moieties like indole, tryptophan can remarkably expand functional structural evolution, which has value for medicinal chemists chemical biologists. The indolyl tryptophan‐ ‐glycosides unique structures biological activities that attracted number studies. Therefore, motifs possessed an extensive interest direction efficient synthesis. Herein, this review systematically summarizes classical ‐heteroaryl glycosides mainly focusing on indole Furthermore, highlighted recently developed metal‐catalyzed C−H functionalization photoinduced cross‐coupling strategies aim control regioselectivity diastereoselectivity reaction In view type, mechanism, status, will cover synthesis diverse regio‐ from four perspectives include a) conventional approach, b) heterocyclization sequence, c) functionalization, d) cross‐coupling. 1. Introduction 2. Strategies 2.1. Conventional approach 2.2. Heterocyclization sequence 2.3. Metal‐catalyzed 2.4. Photoinduced 3. Summary Outlook

Language: Английский

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Recent Advances on the Synthesis of C-Glycosides from 1,2-Glycals

Synthesis, Journal Year: 2023, Volume and Issue: 56(07), P. 1070 - 1096

Published: Dec. 5, 2023

Abstract The development of stereoselective synthetic routes for C-glycosides has attracted immense attention from carbohydrate chemists over the last two decades. In this short review, progress made decade towards synthesis using glycals as precursors is discussed. Glycals have been extensively manipulated to generate oxocarbenium cations or glycosyl anions formation C–C bonds at anomeric position through attack C-nucleophiles via transition-metal-catalyzed coupling reactions. Recent reports on carbon-Ferrier, intramolecular Cope, and Claisen rearrangements, along with various reactions in presence absence directing groups are evaluated herein. Contemporary applications these syntheses natural products, drugs scaffolds bioactive potential briefly 1 Introduction 2 Rearrangement Reactions 2.1 Carbon-Ferrier 2.2 Other 3 C1 Coupling 4 Annulations 5 Addition 6 Natural Product Synthesis 7 Conclusion

Language: Английский

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Catalytic ring-strain release toward a facial and efficient synthesis of versatile C-glycosides

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: unknown, P. 110560 - 110560

Published: Oct. 1, 2024

Language: Английский

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Advances on the Synthesis of C-Aryl-glycosides Since 2019

Synlett, Journal Year: 2024, Volume and Issue: unknown

Published: March 7, 2024

Abstract Aryl-glycosides represent a significant subclass of crucial glycosidic compounds, increasingly capturing the attention pharmaceutical developers as bioelectronic motifs embedded within glycosides. Their outstanding resistance to enzymatic hydrolysis bestows distinctive advantage in field drug development, particularly therapeutic domains such diabetes treatment, where pharmaceuticals based on C-aryl-glycoside architecture manifest compelling efficacy. As result, researchers realm synthetic chemistry have diligently explored and devised plethora streamlined efficacious methodologies. This comprehensive account systematically delineates methodologies employed recent years for efficient synthesis C-aryl-glycosides, offering insights into three primary directions: transition-metal catalysis, radical strategies, metal-free catalysis processes. 1 Introduction 2 Glycosylation via Transition-Metal Catalytic Approaches 3 Glycosyl Radical 4 Metal-Free 5 Conclusion Outlook

Language: Английский

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Five-membered ring systems: Pyrroles and benzo analogs

Progress in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 123 - 173

Published: Jan. 1, 2024

Language: Английский

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Cobalt-Catalyzed Highly α-Stereoselective Glycosylation of Glycals

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 22, 2024

Following the satisfactory catalytic performance of cobalt in

Language: Английский

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