Practical, Multigram Preparation of Synthetically Useful, Enantiomerically Pure Building-Blocks from Quinic Acid

Practical, Multigram Preparation of Synthetically Useful, Enantiomerically Pure Building-Blocks from Quinic Acid

The naturally abundant, enantiomerically pure cyclitol quinic acid has been converted into a synthetically useful enone in nearly quantitative yield using the operationally straightforward and reproducible protocols reported herein. The latter compound, which was obtained in multigram quantities, en...

Full description

Bibliographic Details
Main Authors:	Shen Tan, Ping Lan, Martin G. Banwell, Lorenzo V. White
Format:	Article
Language:	English
Published:	Georg Thieme Verlag KG 2022-11-01
Series:	SynOpen
Subjects:	1,2-addition α,β-annulation cross-coupling cyclohexenone enantiomerically pure α-iodination quinic acid
Online Access:	http://www.thieme-connect.de/DOI/DOI?10.1055/a-1952-4557

Similar Items

One-pot Fluorination and Organocatalytic Robinson Annulation for Asymmetric Synthesis of Mono- and Difluorinated Cyclohexenones
by: Xin Huang, et al.
Published: (2018-09-01)

Novel chitosan-quinic acid nanoparticles labeled with m99 technetium for breast cancer imaging
by: Atousa Zia, et al.
Published: (2022-07-01)

Quinic acid regulated TMA/TMAO-related lipid metabolism and vascular endothelial function through gut microbiota to inhibit atherosclerotic
by: Qiao Jin, et al.
Published: (2024-04-01)

Advances in Production of Hydroxycinnamoyl-Quinic Acids: From Natural Sources to Biotechnology
by: Egle Valanciene, et al.
Published: (2022-12-01)

Molecularly Imprinted Solid Phase Extraction Strategy for Quinic Acid
by: Sarah H. Megahed, et al.
Published: (2022-08-01)

Isolation of quinic acid from dropped Citrus reticulata Blanco fruits: its derivatization, antibacterial potential, docking studies, and ADMET profiling
by: Heena, et al.
Published: (2024-04-01)

Quinic acid ameliorates ulcerative colitis in rats, through the inhibition of two TLR4‐NF‐κB and NF‐κB‐INOS‐NO signaling pathways
by: Maryam Ghasemi‐Dehnoo, et al.
Published: (2023-08-01)

Trans enantiomeric separation of MESA and MOXA, two environmentally important metabolites of the herbicide, metolachlor
by: Marla R. Bianca, et al.
Published: (2022-01-01)

Comparison of Volatile Constituents Present in Commercial and Lab-Distilled Frankincense (<i>Boswellia carteri</i>) Essential Oils for Authentication
by: Pawan Kumar Ojha, et al.
Published: (2022-08-01)

Antiphotoaging Effect of 3,5-Dicaffeoyl-epi-quinic Acid against UVA-Induced Skin Damage by Protecting Human Dermal Fibroblasts In Vitro
by: Jung Hwan Oh, et al.
Published: (2020-10-01)

The Preservation and Enantiomeric Selection of Linalool by Nanoencapsulation Using Cyclodextrins
by: Tanaporn Poonphatanapricha, et al.
Published: (2021-09-01)

Chemical Profiling of Kaliziri Injection and Quantification of Six Caffeoyl Quinic Acids in Beagle Plasma by LC-MS/MS
by: Changhua Liu, et al.
Published: (2022-05-01)

Enantiomeric Ratio of Amino Acids as a Tool for Determination of Aging and Disease Diagnostics by Chromatographic Measurement
by: Květa Kalíková, et al.
Published: (2016-10-01)

Chemical composition, enantiomeric analysis and anticholinesterase activity of Lepechinia betonicifolia essential oil from Ecuador
by: James Calva, et al.
Published: (2022-12-01)

Composition and Enantiomeric Analysis of the Essential Oil of the Fruits and the Leaves of Pistacia vera from Greece
by: Anastasia Tsokou, et al.
Published: (2007-06-01)

Toxicological Evaluation of Novel Cyclohexenone Derivative in an Animal Model through Histopathological and Biochemical Techniques
by: Muhammad Kamil, et al.
Published: (2021-05-01)

α,β-Enone Borylation by Bis(Pinacolato)Diboron Catalyzed by Cu<sub>3</sub>(BTC)<sub>2</sub> Using Cesium Carbonate as a Base
by: Amarajothi Dhakshinamoorthy, et al.
Published: (2021-05-01)

Chiral Analysis of Pesticides and Drugs of Environmental Concern: Biodegradation and Enantiomeric Fraction
by: Alexandra S. Maia, et al.
Published: (2017-09-01)

Altering the Stereoselectivity of Whole-Cell Biotransformations via the Physicochemical Parameters Impacting the Processes
by: Agnieszka Raczyńska, et al.
Published: (2021-06-01)

Effect of the Enantiomeric Ratio of Eutectics on the Results and Products of the Reactions Proceeding with the Participation of Enantiomers and Enantiomeric Mixtures
by: Emese Pálovics, et al.
Published: (2020-09-01)

Chiral Separation of Vildagliptin by Capillary Electrophoresis—The Study of Enantiomeric Complexation
by: Lajos Attila Papp, et al.
Published: (2023-12-01)

Acyl Quinic Acid Derivatives Screened Out from <i>Carissa spinarum</i> by SOD-Affinity Ultrafiltration LC–MS and Their Antioxidative and Hepatoprotective Activities
by: Ye Liu, et al.
Published: (2021-08-01)

Analysis of Volatile Constituents in <i>Curcuma</i> Species, <i>viz. C. aeruginosa</i>, <i>C. zedoaria</i>, and <i>C. longa</i>, from Nepal
by: Darbin Kumar Poudel, et al.
Published: (2022-07-01)

Determination of Enantiomeric Excess by Optofluidic Microlaser near Exceptional Point
by: Zhiyang Xu, et al.
Published: (2024-02-01)

Estimation of Enantiomeric Excess Based on Rapid Host–Guest Exchange
by: Jan Labuta, et al.
Published: (2021-09-01)

Preparation of Enantiomerically Enriched <i>P</i>-Stereogenic Dialkyl-Arylphosphine Oxides via Coordination Mediated Optical Resolution
by: Bence Varga, et al.
Published: (2020-02-01)

Chemical and Biological Activity Profiling of <i>Hedyosmum</i> <i>strigosum</i> Todzia Essential Oil, an Aromatic Native Shrub from Southern Ecuador
by: Luis Cartuche, et al.
Published: (2022-10-01)

The Effect of Enantiomer Elution Order on the Determination of Minor Enantiomeric Impurity in Ketoprofen and Enantiomeric Purity Evaluation of Commercially Available Dexketoprofen Formulations
by: Kenan Can Tok, et al.
Published: (2020-12-01)

A useful quantitative model for determination of enantiomeric composition of racemate praziquantel by ultraviolet spectroscopy combined with partial least squares and its application to praziquantel tablets
by: Man Zhao, et al.
Published: (2018-05-01)

Chiral Monolithic Silica-Based HPLC Columns for Enantiomeric Separation and Determination: Functionalization of Chiral Selector and Recognition of Selector-Selectand Interaction
by: Mufarreh Asmari, et al.
Published: (2021-08-01)

Synthetic Cathinones: Recent Developments, Enantioselectivity Studies and Enantioseparation Methods
by: Ana Sofia Almeida, et al.
Published: (2022-03-01)

Push or Pull for a Better Selectivity? A Study on the Electronic Effects of Substituents of the Pyridine Ring on the Enantiomeric Recognition of Chiral Pyridino-18-Crown-6 Ethers
by: Balázs Szemenyei, et al.
Published: (2020-10-01)

A New Method for Enantiomeric Determination of 3,4-Methylenedioxymethamphetamine and p-Methoxymethamphetamine in Human Urine
by: Wei-Jay Chen, et al.
Published: (2022-01-01)

Rapid Separation of Enantiomeric Impurities in Chiral Molecules by a Self-Referential Weak Measurement System
by: Yang Xu, et al.
Published: (2018-11-01)

Accurate Determination of Enantiomeric Excess Using Raman Optical Activity
by: Pavel Michal, et al.
Published: (2022-05-01)

Study of Different Chiral Columns for the Enantiomeric Separation of Azoles Using Supercritical Fluid Chromatography
by: Laura Toribio, et al.
Published: (2022-12-01)

Elaboration of test for enantiomeric purity determination of chiral monomers of polyamide mimetics of nucleic acids
by: D. I. Prokhorov, et al.
Published: (2010-12-01)

Identification and Bioactivity of Compounds from the Mangrove Endophytic Fungus Alternaria sp.
by: Jinhua Wang, et al.
Published: (2015-07-01)

Evaluation of cytotoxic and apoptogenic effects of chlorogenic acid derivatives from Berberis vulgaris fruits on human breast adenocarcinoma cell line
by: E. Ghafourian, et al.
Published: (2017-11-01)

Friction and wear behavior of commercially pure titanium TA1 at high temperature
by: ZHANG Jia-ming, et al.
Published: (2021-03-01)