Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Rapid, one-pot synthesis of ?-siloxy-?-haloaldehydes.

ABSTRACT: The Mukaiyama cross-aldol reaction of ?-fluoro-, ?-chloro-, and ?-bromoacetaldehyde-derived (Z)-tris(trimethylsilyl)silyl enol ethers is described, furnishing anti-?-siloxy-?-haloaldehydes. A highly diastereoselective, one-pot, sequential double-aldol process is developed, affording novel ?,?-bissiloxy-?,?-bishaloaldehydes. Reactions are catalyzed by C(6)F(5)CHTf(2) and C(6)F(5)CTf(2)AlMe(2) (0.5-1.5 mol %) and provide access to halogenated polyketide fragments.

SUBMITTER: Saadi J

PROVIDER: S-EPMC3181128 | biostudies-literature | 2011 Sep

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Rapid, one-pot synthesis of β-siloxy-α-haloaldehydes.

Saadi Jakub J Akakura Matsujiro M Yamamoto Hisashi H

Journal of the American Chemical Society 20110818 36

The Mukaiyama cross-aldol reaction of α-fluoro-, α-chloro-, and α-bromoacetaldehyde-derived (Z)-tris(trimethylsilyl)silyl enol ethers is described, furnishing anti-β-siloxy-α-haloaldehydes. A highly diastereoselective, one-pot, sequential double-aldol process is developed, affording novel β,δ-bissiloxy-α,γ-bishaloaldehydes. Reactions are catalyzed by C(6)F(5)CHTf(2) and C(6)F(5)CTf(2)AlMe(2) (0.5-1.5 mol %) and provide access to halogenated polyketide fragments. ...[more]

PMID: 21815682

Similar Datasets

Pot economy and one-pot synthesis.

Project description:The one-pot synthesis of a target molecule in the same reaction vessel is widely considered to be an efficient approach in synthetic organic chemistry. In this review, the characteristics and limitations of various one-pot syntheses of biologically active molecules are explained, primarily involving organocatalytic methods as key tactics. Besides catalysis, the pot-economy concepts presented herein are also applicable to organometallic and organic reaction methods in general.

| S-EPMC5529999 | biostudies-other

One-Pot Regiodirected Annulations for the Rapid Synthesis of π-Extended Oligomers.

Project description:We demonstrate the broad applicability of the annulation protocol combining, in one pot, a direct arylation and cross aldol condensation for the straightforward synthesis at gram-scale of π-extended thiophene-based scaffolds. The regiospecific direct arylation drives the subsequent cross-aldol condensation proceed under the same basic conditions, and the overall protocol has broad applicability in the synthesis of extended aromatics wherein the thiophene ring is annulated with furans, pyridines, indoles, benzothiophenes, and benzofurans. These scaffolds can be further elaborated into π-extended, highly fluorescent oligomers with a central deficient benzothiadiazole unit with up to nine aromatic rings through coupling reactions.

| S-EPMC7997634 | biostudies-literature

One-pot synthesis of (-)-Ambrox.

Project description:(-)-Ambrox is recognised as the prototype of all ambergris odorants. Widely used in perfumery, (-)-Ambrox is an important ingredient due to its unique scent and excellent fixative function. An environmentally friendly and practical preparation of (-)-Ambrox is still unavailable at present although a lot of attention has been paid to this hot research topic for many years. A one-pot synthesis of (-)-Ambrox was studied starting from (-)-sclareol through oxidation with hydrogen peroxide in the presence of a quaternary ammonium phosphomolybdate catalyst {[C5H5NC16H33] [H2PMo12O40]}, which gave the product a 20% overall yield.

| S-EPMC5007644 | biostudies-literature

Fluorous-Assisted One-Pot Oligosaccharide Synthesis.

Project description:A new method for oligosaccharide assembly that combines the advantages of one-pot synthesis and fluorous separation is described. After one-pot glycosylations are completed, a fluorous tag is introduced into the reaction mixture to selectively "catch" the desired oligosaccharide, which is rapidly separated from non-fluorous impurities by fluorous solid-phase extraction (F-SPE). Subsequent "release" of the fluo rous tag and F-SPE achieved the purification of the desired oligosaccharide without the use of time- and solvent-consuming silica gel chromatography. Linear and branched oligosaccharides have been synthesized with this approach in just a few hours (for the overall oligosaccharide assembly and purification process).

| S-EPMC3324286 | biostudies-literature

Stereoselective one-pot synthesis of polypropionates.

Project description:Polypropionates-motifs with alternating methyl and hydroxy groups-are important segments of many natural products possessing high bioactivity and therapeutic value. Synthetic access to these structures remains an area of intensive interest, focusing on the establishment of the contiguous stereocentres and a desire for operational simplicity. Here we report an efficient strategy for the stereoselective assembly of polypropionates with three or four stereocentres through a three-step relay process that include Diels-Alder reaction, silylenol ether hydrolysis and Baeyer-Villiger oxidation. The stereochemistry and functionality of the resulting polypropionates depend on the substitution pattern of the diene and dienophile substrates of the Diels-Alder cycloaddition. More importantly, the relay sequence is effectively performed in one pot, and the product could potentially undergo the same sequence for further elaboration. Finally, the C1-C9 segment of the macrolide etnangien is constructed with four of the six stereogenic centres established using the relay sequence.Polypropionates are present in many natural products possessing high bioactivity and therapeutic value. Here the authors show a strategy for the stereoselective assembly of polypropionates with three or four stereocentres through a process that includes a Diels-Alder reaction, silylenol ether hydrolysis and Baeyer-Villiger oxidation.

| S-EPMC5612996 | biostudies-literature

One-pot, three-component arylalkynyl sulfone synthesis.

Project description:A one-pot three-component protocol for the preparation of arylsulfonyl alkynes through the reaction of ethynyl-benziodoxolone (EBX) reagents, DABSO (DABCO·SO2), and either organomagnesium reagents or aryl iodides with a palladium catalyst is reported. A broad range of aryl and heteroarylalkynyl sulfones were obtained in 46-85% overall yield.

| S-EPMC4342956 | biostudies-literature

One-pot catalytic asymmetric synthesis of pyranones.

Project description:Enantioenriched pyranones are important intermediates in the synthesis of natural products and the generation of compound libraries. A one-pot method for their synthesis is outlined. Catalytic asymmetric alkylation of 2-furfurals in the presence of catalytic (-)-MIB generates enantioenriched furyl zinc alkoxides. Addition of water/THF followed by NBS results in formation of pyranones with ee's >90% and yields between 46-77%.

| S-EPMC2709820 | biostudies-literature

One-Pot Catalytic Asymmetric Synthesis of Tetrahydrocarbazoles.

Project description:A one-pot asymmetric synthesis of 1,2,3,4-tetrahydrocarbazoles has been developed via an enantioselective [3 + 3] annulation of 2-alkynylindoles and donor-acceptor cyclopropanes. In the presence of chiral Lewis acids as catalysts, a series of optically active tetrahydrocarbazoles were furnished in high yields (63-87%) with good to excellent levels of enantioselectivity (up to 94% ee).

| S-EPMC4746102 | biostudies-literature

"Chocolate" Gold Nanoparticles-One Pot Synthesis and Biocompatibility.

Project description:The chemical synthesis of nanoparticles can involve and generate toxic materials. Here, we present for the first time, a one pot direct route to synthesize gold nanoparticles (AuNPs) using natural cacao extract as both a reducing and stabilizing agent. The nanoparticles were characterized by UV-visible spectroscopy (UV-VIS), dynamic light scattering (DLS), and transmission electron microscopy (TEM); and have excellent biocompatibility with human primary dermal fibroblasts.

| S-EPMC6071287 | biostudies-other

Hierarchical and programmable one-pot synthesis of oligosaccharides.

Project description:The programmable one-pot oligosaccharide synthesis method was designed to enable the rapid synthesis of a large number of oligosaccharides, using the software Optimer to search Building BLocks (BBLs) with defined relative reactivity values (RRVs) to be used sequentially in the one-pot reaction. However, there were only about 50 BBLs with measured RRVs in the original library and the method could only synthesize small oligosaccharides due to the RRV ordering requirement. Here, we increase the library to include 154 validated BBLs and more than 50,000 virtual BBLs with predicted RRVs by machine learning. We also develop the software Auto-CHO to accommodate more data handling and support hierarchical one-pot synthesis using fragments as BBLs generated by the one-pot synthesis. This advanced programmable one-pot method provides potential synthetic solutions for complex glycans with four successful examples demonstrated in this work.

| S-EPMC6283847 | biostudies-other

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