Paper
Synthetic Studies on Potent Marine Drugs: Synthesis and the Crystal Structure of 6-tert-butyl-4-phenyl-4H-chromene-2-carboxylic Acid
Published Nov 4, 2013 · Hui-Jing Li, Jun-Li Wang, Rui Wang
Journal of Chemistry
Q2 SJR score
22
Citations
0
Influential Citations
Abstract
4H-Chromene-2-carboxylic acid ester derivatives of renieramycin M might be of use for the structural-activity relationship studies of antitumor antibiotic tetrahydroisoquinoline natural products. Accordingly, 6-tert-butyl-4-phenyl-4H-chromene-2-carboxylic acid, one key intermediate, was synthesized via the condensation of (3E)-2-oxo-4-phenylbut-3-enoate methyl ester with 4-tert-butylphenol in the presence of AuCl3/3AgOTf (5 mol%), followed by cyclodehydration and aqueous hydrolysis. The product was unambiguously shown to the 4H-chromene-2-carboxylic acid by spectroscopy and X-ray crystallographic analysis. A packing diagram of the crystal structure shows that aromatic -stacking interactions and O–H⋯O hydrogen bond stabilize the structure in the solid.
Study Snapshot
6-tert-butyl-4-phenyl-4H-chromene-2-carboxylic acid, a key intermediate in the synthesis of antitumor antibiotic tetrahydroisoquinoline natural products, has been synthesized and its crystal structure determined.
PopulationOlder adults (50-71 years)
Sample size24
MethodsObservational
OutcomesBody Mass Index projections
ResultsSocial networks mitigate obesity in older groups.
Sign up to use Study Snapshot
Consensus is limited without an account. Create an account or sign in to get more searches and use the Study Snapshot.
Full text analysis coming soon...
References
Total synthesis of (-)-quinocarcin by gold(I)-catalyzed regioselective hydroamination.
This novel and enantioselective total synthesis of (-)-quinocarcin involves the highly stereoselective preparation of the 2,5-cis-pyrrolidine by intramolecular amination, a selective substrate-controlled 6-endo-dig intramolecular alkyn
2012·53citations·Hiroaki Chiba et al.·Angewandte Chemie
Angewandte Chemie
Chemistry of renieramycins. Part 12: An improved total synthesis of (±)-renieramycin G
This improved total synthesis of ()-renieramycin G from readily available 2-hydroxy-3-methyl-4,5-dimethoxybenzaldehyde in 21 steps (6.3% overall yield) features a concise pentacyclic framework construction and cytotoxicity studies.
2012·16citations·M. Yokoya et al.·Tetrahedron
Tetrahedron
Total synthesis and cytotoxicity of (−)-jorumycin and its analogues
()-jorumycin and its analogues show similar cytotoxicity to ()-jorumycin, with hippuric acid ester derivative 23 showing the most potent and broad-spectrum cytotoxic activity against ten cell lines.
2012·26citations·W. Liu et al.·Tetrahedron
Tetrahedron
Chemistry of renieramycins. Part 11: Total synthesis of (±)-cribrostatin 4
This study presents a 19-step synthesis of ()-cribrostatin 4 from piperazine-2,5-dione derivative 6 and its cytotoxicity studies.
2011·20citations·M. Yokoya et al.·Tetrahedron
Tetrahedron
Facile Synthesis of Spiropyrans from Chromene Hemiacetal Esters and Bifunctional Nucleophiles
This study demonstrates a facile synthesis of new spiropyrans using chromene hemi-acetal esters and bifunctional nucleophiles, making previously unpractical amination and amidation processes practical.
2011·11citations·Yan‐Chao Wu et al.·Synlett
Synlett
Asymmetric total synthesis of (-)-saframycin A from L-tyrosine.
The asymmetric total synthesis of (-)-saframycin A from L-tyrosine in 24 steps with 9.7% overall yield shows high selectivity and efficiency in the synthesis of this natural antitumor product.
2011·35citations·Wenfang Dong et al.·The Journal of organic chemistry
The Journal of organic chemistry
Asymmetric [C + NC + CC] coupling entry to the naphthyridinomycin natural product family: formal total synthesis of cyanocycline A and bioxalomycin β2.
The asymmetric [C + NC + CC] coupling reaction effectively synthesized cyanocycline A and bioxalomycin 2, reducing the number of steps needed to assemble complex molecular targets by one-third.
2011·17citations·P. Garner et al.·The Journal of organic chemistry
The Journal of organic chemistry
Chemistry of renieramycins. Part 9: Stereocontrolled total synthesis of (±)-renieramycin G
This study presents a 25-step stereocontrolled total synthesis of ()-renieramycin G from readily available 2-hydroxy-3-methyl-4,5-dimethoxybenzaldehyde, highlighting its efficient construction and base-catalyzed isomerization.
2011·20citations·M. Yokoya et al.·Tetrahedron Letters
Tetrahedron Letters
Cascade reaction of β,γ-unsaturated α-ketoesters with phenols in trityl chloride/TFA system. Highly selective synthesis of 4-aryl-2H-chromenes and their applications.
This study demonstrates a highly selective synthesis of 4-aryl-2H-chromenes using a Friedel-Crafts alkylation/cyclodehydration process, with potential applications in organic synthesis and catalysis.
2011·18citations·Yan‐Chao Wu et al.·Organic & biomolecular chemistry
Organic & biomolecular chemistry
Citations
Structure modification and anti-tumor activity evaluation on sesquiterpene lactones TBA and TBB from Sphagneticola trilobata
Sesquiterpene lactone derivatives from Sphagneticola trilobata show weaker anti-tumor activity compared to their parental compounds, making them less promising for cancer treatment.
2022·2citations·Xiu-jia Zhou et al.·Natural Product Research
Natural Product Research
Characterisation techniques for analysis of imidazolium-based ionic liquids and application in polymer preparation: A review
This paper reviews the characterisation analysis of imidazolium-based ionic liquids and their potential applications in polymer preparation, highlighting their low viscosity, low melting points, and high stability.
2021·43citations·N. Noorhisham et al.·Journal of Molecular Liquids
Journal of Molecular Liquids
Distribution, source identification, and assessment of heavy metal pollution in the surface and pore waters of Cipeles River, West Java, Indonesia
Heavy metal pollution in Cipeles River is mainly caused by iron and manganese from soil run-off, with significant correlation between pore and surface water concentrations.
2020·10citations·D. R. Wulan et al.·Environmental Science and Pollution Research
Environmental Science and Pollution Research
A comprehensive review of ethnopharmacological uses, phytochemistry, biological activities, and future prospects of Nigella glandulifera
Nigella glandulifera has traditional uses in treating endocrine, respiratory, urogenital, and nervous system diseases with minimal toxicity, offering potential for future research.
2020·14citations·Yunliang Zheng et al.·Medicinal Chemistry Research
Medicinal Chemistry Research
Distribution, speciation and risk assessment of heavy metals: geochemical exploration of Gulf of Kachchh, Gujarat, India
Heavy metal contamination in the Gulf of Kachchh is mainly due to industrialization and domestic waste, with Cu contamination on the rise, posing a major ecological risk.
2020·15citations·Haresh Z. Panseriya et al.·Environmental Earth Sciences
Environmental Earth Sciences
Distribution, Ecological Risk Assessment, and Source Identification of Heavy Metals in River Sediments from Hai River and Its Tributaries, Tianjin, China
Cd contributes over 50% of the ecological risk in the Hai River and its tributaries, with Cu and Cd mainly derived from anthropogenic sources, and overlying water quality influences heavy metal distribution.
2020·19citations·Mengxin Kang et al.·Water, Air, & Soil Pollution
Water, Air, & Soil Pollution
Comprehensive utilization of edible mushroom Auricularia auricula waste residue—Extraction, physicochemical properties of melanin and its antioxidant activity
Ultrasonic-assisted extraction of melanin from Auricularia auricula waste residue effectively extracts melanin, which has antioxidant properties and protects cells from oxidative damage caused by H2O2.
2019·25citations·Xin Liu et al.·Food Science & Nutrition
Food Science & Nutrition
Cadmium bioaccumulation in Lamellidens marginalis and human health risk assessment: A case study in India
Cadmium bioaccumulation in Lamellidens marginalis mussels poses a high health risk to humans, with low-income and older individuals living near East Kolkata Wetlands at high risk.
2018·9citations·Santu Ghosh et al.·Human and Ecological Risk Assessment: An International Journal
Human and Ecological Risk Assessment: An International Journal