Recent asymmetric synthesis of natural products bearing an α-tertiary amine moiety via temporary chirality induction strategies

Abstract

This review highlights recent advances in the asymmetric synthesis of α-tertiary amine natural products via temporary chirality induction methods: Seebach's self-regeneration of stereocenters, C-to-N-to-C chirality transfer, and memory of chirality.

Antimicrobial Activity of Trigonelline Hydrochloride Against Pseudomonas aeruginosa and Its Quorum-Sensing Regulated Molecular Mechanisms on Biofilm Formation and Virulence

“…For instance, P. aeruginosa under environmental stress develops biofilms as a survival strategy, which helps in escaping the host barrier and antimicrobial threats and thus results in higher aggressiveness. − Plant-derived products are being used ethnically for centuries to combat pathogens and are now being considered as a major source of alternate therapeutic chemical leads. − Trigonelline, a pyridine alkaloid, has been reported to have pharmacological importance for its antioxidant features. − In this study, the antibacterial activity of TH was analyzed using P. aeruginosa PAO1 as the model organism.…”

“…Emergence of multidrug resistance cases in an alarming rate calls the need to search for alternative therapeutic ways to combat biofilm formation ability and to quench QS-system. Plant-derived products are being used for centuries to combat pathogens, − and sometimes they are used in combination with traditional antibiotics to increase efficiency. , Among such phytochemicals, alkaloids are vastly reported to have antimicrobial activity. , Trigonelline is a pyridine alkaloid, a derivative of vitamin B3 (niacin) with a chemical formula of C 7 H 7 NO 2 , and is generally found in fenugreek (Trigonella foenum-graecum L.) belonging to family Fabaceae, a traditional spice crop reported to have ethnomedicinal usages . Other than fenugreek, trigonelline is also found in some plants such as Allium cepa, Pisum sativum, Coffea sp., Zea mays, Hordeum vulgare, Lycopersicon esculentum, Glycine max, and in a red algae Pterocladiella capillacea. , …”

Simplified Modular Access to Enantiopure 1,2-Aminoalcohols via Ni-Electrocatalytic Decarboxylative Arylation

“…Subsequent reactions (both radical and polar bond formations) at the C-terminus generally take place with near-complete stereocontrol to “regenerate” the original stereocenter in a predictable way. The SRS approach has been applied in numerous contexts over the years, , although its use in radical chemistry has seen only limited applications. Indeed, several examples of intramolecular radical C–C bond formation have been reported. , Intermolecular C–C bond formations in this context are all reliant on Giese-type additions − to electron-deficient olefins such as Inoue’s acyltellurium studies .…”