Optimization of Manganese Coupling Reaction for Kilogram-Scale Preparation of Two Aryl-1,3-dione Building Blocks

2017 ◽  
Vol 21 (10) ◽  
pp. 1625-1632 ◽  
Author(s):  
Tomas Smejkal ◽  
Vijayagopal Gopalsamuthiram ◽  
Sujit K. Ghorai ◽  
Anup M. Jawalekar ◽  
Dinesh Pagar ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Building Blocks ◽  
Scale Preparation

scholarly journals Fluorinated Iron(ii) clathrochelate units in metalorganic based copolymers: improved porosity, iodine uptake, and dye adsorption properties

RSC Advances ◽  
2021 ◽  
Vol 11 (25) ◽  
pp. 14986-14995
Author(s):  
Suchetha Shetty ◽  
Noorullah Baig ◽  
Atikur Hassan ◽  
Saleh Al-Mousawi ◽  
Neeladri Das ◽  
...  
Keyword(s):  
Dye Adsorption ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Building Blocks ◽  
Adsorption Properties ◽  
Iodine Uptake ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed

We report the synthesis of metalorganic copolymers made from the palladium catalyzed Sonogashira cross-coupling reaction between various iron(ii) clathrochelate building blocks with diethynyl–triptycene and fluorene derivatives.

Pyrido[1,2-a]pyrazine - Startprodukte für regioselektive Ringtransformationen und supramolekulare Architekturen / Pyrido[1,2-a]pyrazines - Starting Materials for Regioselective Ringtransformation Reactions and Supramolecular Architectures

2002 ◽  
Vol 57 (4) ◽  
pp. 471-478 ◽  
Author(s):  
D. Müller ◽  
B. Frank ◽  
R. Beckert ◽  
H. Görls
Keyword(s):  
Cycloaddition Reaction ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Building Blocks ◽  
Ring Transformation ◽  
Supramolecular Architectures ◽  
Cross Coupling Reaction ◽  
Metal Catalyzed

The easily available pyrido[1,2-a]pyrazines of type 1 are versatile building blocks for ring transformation reactions.W ith heterocyclic quinones such as quinoline-2,5,8-triones 4a-c, a highly regioselective [4+2]-cycloaddition reaction takes place in the first step, followed by a ring transformation cascade.T he 1,6-diazaanthracene-2,9,10-triones 5a-e, which possess an additional bipyridine substructure, could be isolated as main products.In order to modify the starting products of type 1, a metal-catalyzed cross-coupling reaction with acetylenic benzoic esters 9a,b has been performed.T he modified pyridopyrazines 10a,b which were obtained in good yields could be transformed by analogy to 1a,b into ring-fused heterocyclic quinones 12a,b.

An Efficient Synthesis of the Pentasaccharide Repeating Unit of Pseudomonas aeruginosa Psl Exopolysaccharide

Synlett ◽  
2019 ◽  
Vol 31 (05) ◽  
pp. 469-474 ◽  
Author(s):  
Fruzsina Demeter ◽  
Margaret Dah-Tsyr Chang ◽  
Yuan-Chuan Lee ◽  
Anikó Borbás ◽  
Mihály Herczeg
Keyword(s):  
Pseudomonas Aeruginosa ◽  
Coupling Reaction ◽  
Building Blocks ◽  
Bacterial Biofilm ◽  
Efficient Synthesis ◽  
Negative Bacterium ◽  
Resistant Species ◽  
Promising Therapeutic Target ◽  
Polysaccharide Synthesis ◽  
Life Threatening

Pseudomonas aeruginosa is a biofilm-forming Gram-negative bacterium and a leading cause of life-threatening nosocomial infections. The polysaccharide synthesis locus (Psl) exopolysaccharide of P. aeruginosa is a key constituent of the defending bacterial biofilm layer and is a promising therapeutic target for resistant species. The Psl exopolysaccharide is built up from repeating pentasaccharide units which contain one α- and two β-mannosidic linkages, and one l-rhamnose and one d-glucose moieties. The preparation of this pentasaccharide was first described by Boons et al. in a 34-step synthesis. Based on their work, we have developed a new and effective pathway for the synthesis of the repeating pentasaccharide unit of the Psl exopolysaccharide. We have succeeded in simplifying the synthesis of the l-rhamnose and the α-selective d-mannose building blocks. Furthermore, taking advantage of a chemoselective pre-activation-based β-mannosylation, we directly prepare a thioglycoside disaccharide donor and use it in the next coupling reaction without further transformation. The pentasaccharide, in the form of a p-methoxyphenyl glycoside, is prepared in 26 steps, which is suitable for biological testing.

Synthesis of Useful Benzocyclobutene Building Blocks via the Suzuki-Miyaura Coupling Reaction

Synthesis ◽  
2001 ◽  
Vol 2001 (13) ◽  
pp. 1932-1934 ◽  
Author(s):  
Sambasivarao Kotha ◽  
Kakali Lahiri (née Chakraborty) ◽  
Nampally Sreenivasachary
Keyword(s):  
Coupling Reaction ◽  
Building Blocks

Pd-Catalyzed Cross-Coupling Reaction of Sterically Hindered Vinyl Iodides and Organozinc Reagents. Synthesis of Vitamin D Analogues with an Aromatic Ring Attached at C-17

2002 ◽  
Vol 67 (11) ◽  
pp. 1658-1668 ◽  
Author(s):  
Agnieszka Przezdziecka ◽  
Alicja Kurek-Tyrlik ◽  
Jerzy Wicha
Keyword(s):  
Vitamin D ◽  
Butyl Ester ◽  
Acid Methyl Ester ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Building Blocks ◽  
Vitamin D Analogues ◽  
Aryl Bromides ◽  
Palladium Catalyzed ◽  
Organozinc Reagents

Palladium-catalyzed coupling of steroid 17-iodo-6β-methoxy-3α,5-cyclo-5α-androst-16-ene (4) 17-iodoandrosta-5,16-dien-3β-ol (5), and structurally similar (3aS,7R,7aR)-benzenesulfonyl-3-iodo-3a-methyl-3a,4,5,6,7,7a-hexahydro-1H-indene (6) with various arylzinc chlorides, which were generated from aryl bromides 8 [1-bromomethylbenzene (8a), O-(triethylsilyl-2-bromophenyl)propan-2-ol (8b), 2-(4-bromophenyl)propan-2-ol (8c), 4-bromobenzonitrile (8d), 4-bromobenzoic acid methyl ester (8e), 4-bromobenzoic acid tert-butyl ester (8f) and 3-bromopyridine (8g)] via aryllihium derivatives (the Negishi coupling) was examined. The respective cross-coupling products were obtained in good yields for all aryl bromides except of 8c and 8e. Building blocks for synthesis of certain vitamin D analogues have been prepared.

scholarly journals Erratum: Synthesis of most polyene natural product motifs using just 12 building blocks and one coupling reaction

2014 ◽  
Vol 6 (7) ◽  
pp. 650-650 ◽  
Author(s):  
Eric M. Woerly ◽  
Jahnabi Roy ◽  
Martin D. Burke
Keyword(s):  
Natural Product ◽  
Coupling Reaction ◽  
Building Blocks

scholarly journals Synthesis and Characterization of Metallo-Supramolecular Polymers Based on Benzodipyrrolidone

2021 ◽  
Vol 9 ◽  
Author(s):  
Zheng Chi ◽  
Hao Dong ◽  
Ganhui Shi ◽  
Pan Liu ◽  
Chenchen Ma ◽  
...  
Keyword(s):  
Charge Transfer ◽  
Self Assembly ◽  
Energy Gap ◽  
Coupling Reaction ◽  
Building Blocks ◽  
Supramolecular Polymers ◽  
Absorption Bands ◽  
Suzuki Coupling Reaction ◽  
Ligand Charge Transfer ◽  
Common Precursor

A simple route to the preparation of benzodipyrrolidone (BDP) based monomeric building blocks containing 2,2′:6′,2″-terpyridines is reported from a common precursor 4′-(4-pinacolatoboronphenyl)-2,2′:6′,2″-terpyridine via Suzuki coupling reaction. Self-assembly polymerization with ruthenium (II) ions under mild conditions yielded a series of novel metallo-supramolecular polymers with weak donor-acceptor (D-A) structures based on benzodipyrrolidone. The structure of the bridge connected BDP with terpyridine have a significant impact on the wavelength and intensity of the intramolecular charge transfer (ICT) absorption peak. The resulting metallo-polymers exhibited strong double absorption bands around 315 nm and 510 nm involved in π-π* transitions and ICT or metal to ligand charge transfer (MLCT) absorption bands. The forming of D-A structure and coordination with ruthenium (II) ions is favorable to narrow the energy gap and the energy gaps of the resulting metallo-supramolecular polymers are 2.01 and 1.62 eV, respectively.

scholarly journals Concise Synthesis and Antimicrobial Evaluation of the Guanidinium Alkaloid Batzelladine D

2019 ◽  
Author(s):  
You-Chen Lin ◽  
Aubert Ribaucourt ◽  
Yasamin Moazami ◽  
Joshua Pierce
Keyword(s):  
Antimicrobial Activity ◽  
Late Stage ◽  
Building Blocks ◽  
Controlled Synthesis ◽  
Scale Preparation ◽  
Antimicrobial Evaluation ◽  
Coupling Partner

A concise synthesis of the tricyclic guanidinium alkaloid batzelladine D has been accomplished in a sequence of 8 steps from readily available building blocks. Highlights of the synthesis include gram-scale preparation of a late stage intermediate, pinpoint stereocontrol around the tricyclic skeleton and a modular strategy that enables analog generation. A key bicyclic b-lactam intermediate serves to not only control stereochemistry, but also serves as a pre-activated coupling partner to install the ester sidechain. The stereo-controlled synthesis allowed for the investigation of the antimicrobial activity of batzelladine D, demonstrating promising activity that is more potent for non-natural stereoisomers.

Large scale preparation of chiral building blocks for the P3 site of renin inhibitors

1994 ◽  
Vol 2 (6) ◽  
pp. 403-410 ◽  
Author(s):  
Stephan Doswald ◽  
Heinrich Estermann ◽  
Ernst Kupfer ◽  
Heinz Stadler ◽  
Willi Walther ◽  
...  
Keyword(s):  
Large Scale ◽  
Building Blocks ◽  
Renin Inhibitors ◽  
Large Scale Preparation ◽  
Scale Preparation
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