Category Ranking
98%
Total Visits
921
Avg Visit Duration
2 minutes
Citations
20
Article Abstract
An isothiourea-catalysed enantioselective synthesis of novel tetrahydroindolizine derivatives is reported through a one-pot tandem sequential process. The application of 2-(pyrrol-1-yl)acetic acid in combination with either a trifluoromethyl enone or an α-keto-β,γ-unsaturated ester in an enantioselective Michael addition-lactonisation process, followed by ring-opening and cyclisation, led to a range of 24 tetrahydroindolizine derivatives containing three stereocentres in up to >95 : 5 dr and >99 : 1 er.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8152628 | PMC |
| http://dx.doi.org/10.1039/d0sc00432d | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Enantiospecific Synthesis of Tetrahydroindolizines from Spiro-cyclopropanecarboxylated Sugars.
J Org Chem
January 2025
School of Chemistry, University of Hyderabad, C. R. Rao Road, Gachibowli, Hyderabad 500 046, India.
A facile two-step enantiospecific synthesis of 5,6,7,8-tetrahydroindolizine scaffolds has been developed via TMSOTf-promoted [3 + 2] cycloaddition between carbohydrate-derived spirocyclic donor-acceptor cyclopropanecarboxlates and alkyl/aryl nitriles followed by an intramolecular Mitsunobu reaction of the resulting chiral 2/5-(4-hydroxybutyl)pyrrole derivatives.
View Article and Find Full Text PDFHydrazone Activation in the Aminocatalytic Cascade Reaction for the Synthesis of Tetrahydroindolizines.
Org Lett
February 2024
Institute of Organic Chemistry, Lodz University of Technology, Żeromskiego 116, 90-924 Łódź, Poland.
In this Letter, we demonstrate the usefulness of hydrazone activation for the synthesis of biologically relevant tetrahydroindolizines. A pyrrol-derived hydrazone bearing a Michael acceptor moiety in the -alkyl side chain has been designed with the aim of participating in the aminocatalytic cascade reaction leading to the annulation of the new six-membered heterocyclic scaffold. The application of ()-(-)-α,α-diphenyl-2-pyrrolidinemethanol trimethylsilyl ether as the aminocatalyst allows for the iminium ion-enamine-mediated cascade to proceed in a fully stereoselective manner.
View Article and Find Full Text PDFVisible light-enabled synthesis of phosphorylated indolizine and pyridoindole derivatives HAT-mediated radical cascade cyclization.
Org Biomol Chem
December 2023
Green Pharmaceutical Technology Key Laboratory of Luzhou City, Central Nervous System Drug Key Laboratory of Sichuan Province, School of Pharmacy, Southwest Medical University, Luzhou, 646000, China.
A visible light-enabled cascade cyclization strategy is disclosed with concomitant phosphorylation and heterocycle construction. It provides a novel and environmentally benign approach for accessing tetrahydroindolizine-containing phosphonates under metal-free conditions. Mechanistic studies revealed that phosphinoyl radicals were generated from H-phosphonates a HAT process.
View Article and Find Full Text PDFDiversified Transformations of Tetrahydroindolizines to Construct Chiral 3-Arylindolizines and Dicarbofunctionalized 1,5-Diketones.
J Am Chem Soc
September 2020
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. China.
Enantioselective diverse synthesis of a small-molecule collection with structural and functional similarities or differences in an efficient manner is an appealing but formidable challenge. Asymmetric preparation and branching transformations of tetrahydroindolizines in succession present a useful approach to the construction of -heterocycle-containing scaffolds with functional group, and stereochemical diversity. Herein, we report a breakthrough toward this end via an initial diastereo- and enantioselective [3 + 2] cycloaddition between pyridinium ylides and enones, following diversified sequential transformations.
View Article and Find Full Text PDFSynthesis of 2-phenyl-5,6,7,8-tetrahydroquinoxaline derivatives and screening for P2X1-purinoceptor antagonist activity in isolated preparations of rat vas deferens, for translation into a male contraceptive†.
Biol Reprod
August 2020
Drug Discovery Biology, Monash Institute of Pharmaceutical Sciences, Monash University, Parkville, Victoria. Australia.
Sympathetically mediated contractions of smooth muscle cells in the vasa deferentia are mediated by neuronally released adenosine 5'-triphosphate (ATP) and noradrenaline, which stimulate P2X1-purinoceptors and α1A-adrenoceptors, respectively. This process is crucial for sperm transport, as demonstrated in knockout mouse studies where simultaneous genetic deletion of P2X1-purinoceptors and α1A-adrenoceptors resulted in male infertility. We hypothesize that dual pharmacological antagonism of these two receptors could inhibit sperm transport sufficiently to provide a novel nonhormonal method of male contraception.
View Article and Find Full Text PDF