Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Selective synthesis of 3-formylbenzofuran and 3-acylbenzofuran using a chalcone rearrangement strategy.

ABSTRACT: We developed a method for highly selective synthesis of two benzofuran isomers, by rearranging and subsequently transforming 2-hydroxychalcones. Depending on the reaction conditions, synthesis of 3-formylbenzofurans, unconventional products, and 3-acylbenzofurans was achieved through cyclized 2,3-dihydrobenzofurans obtained from the rearranged products. The facile synthesis of 3-formylbenzofurans facilitated synthesis of the natural product, puerariafuran, from the corresponding chalcone.

SUBMITTER: Nakamura A

PROVIDER: S-EPMC9593264 | biostudies-literature | 2022 Oct

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Selective synthesis of 3-formylbenzofuran and 3-acylbenzofuran using a chalcone rearrangement strategy.

Nakamura Akira A Imamiya Akira A Ikegami Yuichiro Y Rao Fei F Yuguchi Harumi H Miki Yasuyoshi Y Maegawa Tomohiro T

RSC advances 20221025 47

We developed a method for highly selective synthesis of two benzofuran isomers, by rearranging and subsequently transforming 2-hydroxychalcones. Depending on the reaction conditions, synthesis of 3-formylbenzofurans, unconventional products, and 3-acylbenzofurans was achieved through cyclized 2,3-dihydrobenzofurans obtained from the rearranged products. The facile synthesis of 3-formylbenzofurans facilitated synthesis of the natural product, puerariafuran, from the corresponding chalcone. ...[more]

PMID: 36337936

Similar Datasets

Asymmetric Enzymatic Synthesis of Allylic Amines: A Sigmatropic Rearrangement Strategy.

Project description:Sigmatropic rearrangements, while rare in biology, offer opportunities for the efficient and selective synthesis of complex chemical motifs. A "P411" serine-ligated variant of cytochrome P450(BM3) has been engineered to initiate a sulfimidation/[2,3]-sigmatropic rearrangement sequence in whole E. coli cells, a non-natural function for any enzyme, providing access to enantioenriched, protected allylic amines. Five mutations in the enzyme substantially enhance its activity toward this new function, demonstrating the evolvability of the catalyst toward challenging nitrene transfer reactions. The evolved catalyst additionally performs the highly enantioselective imidation of non-allylic sulfides.

| S-EPMC4818679 | biostudies-literature

Selective synthesis of functionalized, tertiary silanes by diastereoselective rearrangement-addition.

Project description:[reaction: see text] Treatment of hydroxy-substituted silyl epoxides with Grignard reagents induces a 1,2-carbon shift to reveal alpha-silyl aldehydes, which are trapped by highly diastereoselective addition reactions of the Grignard reagent. The starting epoxides are readily accessible from propargylic alcohols by regio- and diastereoselective hydrosilylation and epoxidation reactions. In addition to providing functionalized tertiary silane products, the method is shown to offer a tertiary olefin synthesis through chemo- and diastereoselective Peterson elimination of the product tertiary silane diols.

| S-EPMC2509579 | biostudies-literature

Enantioselective Total Synthesis of (-)-Hunterine A Enabled by a Desymmetrization/Rearrangement Strategy.

Project description:The first enantioselective total synthesis of (-)-hunterine A is disclosed. Our strategy employs a catalytic asymmetric desymmetrization of a symmetrical diketone and subsequent Beckmann rearrangement to construct a 5,6-α-aminoketone. A convergent 1,2-addition joins a vinyl dianion nucleophile and the enantioenriched ketone. The endgame of the synthesis features an aza-Cope/Mannich reaction and azide-olefin dipolar cycloaddition to complete the pentacyclic ring system. The synthesis is completed through a regioselective aziridine ring opening.

| S-EPMC10885145 | biostudies-literature

High-throughput synthesis of nanoparticles using oscillating feedback microreactors: a selective scaling-out strategy.

Project description:High-throughput synthesis of high-quality nanoparticles using traditional methods is difficult because of the complexities in controlling residence time and concentration. Passive oscillating feedback micromixers (OFMs) can overcome these difficulties. However, it remains a challenge to significantly increase throughput while retaining the microfluidic advantages. In this work, a selective scaling-out strategy was used to generate a series of enlarged OFMs, which were demonstrated to produce BaSO4 nanoparticles. A novel chaotic convection synthesis mode was found to produce high-quality BaSO4 nanoparticles (mean size, 24.91 nm; size distribution, 10-50 nm) at a high throughput of 281.4 mL min-1. The NP production rate can reach 538.4 g h-1, far exceeding the reported production rates.

| S-EPMC10711568 | biostudies-literature

A conserved strategy of chalcone isomerase-like protein to rectify promiscuous chalcone synthase specificity.

Project description:Land plants produce diverse flavonoids for growth, survival, and reproduction. Chalcone synthase is the first committed enzyme of the flavonoid biosynthetic pathway and catalyzes the production of 2',4,4',6'-tetrahydroxychalcone (THC). However, it also produces other polyketides, including p-coumaroyltriacetic acid lactone (CTAL), because of the derailment of the chalcone-producing pathway. This promiscuity of CHS catalysis adversely affects the efficiency of flavonoid biosynthesis, although it is also believed to have led to the evolution of stilbene synthase and p-coumaroyltriacetic acid synthase. In this study, we establish that chalcone isomerase-like proteins (CHILs), which are encoded by genes that are ubiquitous in land plant genomes, bind to CHS to enhance THC production and decrease CTAL formation, thereby rectifying the promiscuous CHS catalysis. This CHIL function has been confirmed in diverse land plant species, and represents a conserved strategy facilitating the efficient influx of substrates from the phenylpropanoid pathway to the flavonoid pathway.

| S-EPMC7018950 | biostudies-literature

On-surface synthesis of non-benzenoid conjugated polymers by selective atomic rearrangement of ethynylarenes.

Project description:Here, we report a new on-surface synthetic strategy to precisely introduce five-membered units into conjugated polymers from specifically designed precursor molecules that give rise to low-bandgap fulvalene-bridged bisanthene polymers. The selective formation of non-benzenoid units is finely controlled by the annealing parameters, which govern the initiation of atomic rearrangements that efficiently transform previously formed diethynyl bridges into fulvalene moieties. The atomically precise structures and electronic properties have been unmistakably characterized by STM, nc-AFM, and STS and the results are supported by DFT theoretical calculations. Interestingly, the fulvalene-bridged bisanthene polymers exhibit experimental narrow frontier electronic gaps of 1.2 eV on Au(111) with fully conjugated units. This on-surface synthetic strategy can potentially be extended to other conjugated polymers to tune their optoelectronic properties by integrating five-membered rings at precise sites.

| S-EPMC9906656 | biostudies-literature

Discovery of Novel Bacterial Chalcone Isomerases by a Sequence-Structure-Function-Evolution Strategy for Enzymatic Synthesis of (S)-Flavanones.

Project description:Chalcone isomerase (CHI) is a key enzyme in the biosynthesis of flavonoids in plants. The first bacterial CHI (CHIera ) was identified from Eubacterium ramulus, but its distribution, evolutionary source, substrate scope, and stereoselectivity are still unclear. Here, we describe the identification of 66 novel bacterial CHIs from Genbank using a novel Sequence-Structure-Function-Evolution (SSFE) strategy. These novel bacterial CHIs show diversity in substrate specificity towards various hydroxylated and methoxylated chalcones. The mutagenesis of CHIera according to the substrate binding models of these novel bacterial CHIs resulted in several variants with greatly improved activity towards these chalcones. Furthermore, the preparative scale conversion catalyzed by bacterial CHIs has been performed for five chalcones and revealed (S)-selectivity with up to 96 % ee, which provides an alternative biocatalytic route for the synthesis of (S)-flavanones in high yields.

| S-EPMC8361940 | biostudies-literature

Selective inhibition of PARP10 using a chemical genetics strategy.

Project description:The lack of inhibitors that are selective for individual poly-ADP-ribose polymerase (PARP) family members has limited our understanding of their roles in cells. Here, we describe a chemical genetics approach for generating selective inhibitors of an engineered variant of PARP10. We synthesized a series of C-7 substituted 3,4-dihydroisoquinolin-1(2H)-one (dq) analogues designed to selectively inhibit a mutant of PARP10 (LG-PARP10) that contains a unique pocket in its active site. A dq analogue containing a bromo at the C-7 position demonstrated a 10-fold selectivity for LG-PARP10 compared to its WT counterpart. This study provides a platform for the development of selective inhibitors of individual PARP family members that will be useful for decoding their cellular functions.

| S-EPMC4607647 | biostudies-literature

ESD for Colorectal LSL Using a Selective Strategy - a Prospective Cohort Study

Project description:Colonic Laterally spreading lesions (LSL) => 20mm are at high risk to progress to cancer. Overt stigmata of submucosal invasive cancer (SMIC) has been well characterized and includes ulceration and surface pit pattern changes as per the Kudo classification of type V. In a recent report, risk factors for LSL with SMIC and no overt stigmata (i.e. covert SMIC) were described. Resection of these lesions ‘en-bloc’ can allow for better histological staging and potentially reduce the need for surgical resection.

| 2310041 | ecrin-mdr-crc

Unified synthesis of caged Garcinia natural products based on a site-selective Claisen/Diels-Alder/Claisen rearrangement.

Project description:A unified synthetic strategy toward caged Garcinia natural products has been designed and implemented. Central to the strategy is a tandem Claisen/Diels-Alder/Claisen rearrangement of a suitably substituted xanthone precursor to form forbesione (1a). Serving as a template, forbesione is then used to deliver representative members of this family, including desoxygaudichaudione A (4), desoxymorellin (5), and gambogin (10). Studies on the timing of this reaction cascade suggest that the C-ring Claisen/Diels-Alder rearrangement proceeds initially and is followed by the A-ring Claisen reaction. The electronic and steric effects that govern the outcome of this cascade are presented.

| S-EPMC514429 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data