A5019270042- Synthesis and Catalytic Reactions
- Catalytic C–H Functionalization Methods
- Synthetic Organic Chemistry Methods
- Chemical Synthesis and Analysis
- X-ray Diffraction in Crystallography
- Sulfur-Based Synthesis Techniques
- Crystallization and Solubility Studies
- Carbohydrate Chemistry and Synthesis
- Sphingolipid Metabolism and Signaling
- Chemical Reactions and Mechanisms
- Radical Photochemical Reactions
- Advanced Synthetic Organic Chemistry
- Microbial Natural Products and Biosynthesis
- Catalytic Alkyne Reactions
- Asymmetric Hydrogenation and Catalysis
- Organoboron and organosilicon chemistry
- Coordination Chemistry and Organometallics
- Bioactive Compounds and Antitumor Agents
- Marine Sponges and Natural Products
- Phenothiazines and Benzothiazines Synthesis and Activities
- Oxidative Organic Chemistry Reactions
- Chemical synthesis and alkaloids
- Fluorine in Organic Chemistry
- Amino Acid Enzymes and Metabolism
- Traditional and Medicinal Uses of Annonaceae
UCB Pharma (United Kingdom)
2020
Universitat Rovira i Virgili
2008-2016
University of Bristol
2015-2016
Max-Planck-Institut für Kohlenforschung
2013-2014
Universidad de Huelva
2010-2014
Max Planck Society
2013
Boston College
2011
The generation of carbon radicals by halogen-atom and group transfer reactions is generally achieved using tin silicon reagents that maximize the interplay enthalpic (thermodynamic) polar (kinetic) effects. In this work, we demonstrate a distinct reactivity mode enabled quantum mechanical tunneling uses cyclohexadiene derivative γ-terpinene as abstractor under mild photochemical conditions. This protocol activates alkyl aryl halides well several alcohol thiol derivatives. Experimental...
A protocol for the stereospecific coupling of chiral secondary and tertiary boronic esters with lithiated N-heteroaromatics is described. The process involves initial boronate complex formation followed by addition Troc-Cl, which activates nitrogen induces 1,2-migration. Oxidative workup furnishes coupled product >98% es.
A new generation of alkyne metathesis catalysts, which are distinguished by high activity and an exquisite functional group tolerance, allows the scope this transformation to be extended beyond its traditional range. They accept substrates that were previously found problematic or unreactive, such as propargyl alcohol derivatives, electron-deficient electron-rich acetylenes various types, even terminal alkynes. Moreover, post-metathetic transformations other than semi-reduction increase...
Silver complexes bearing trispyrazolylborate ligands (Tp(x)) catalyze the aziridination of 2,4-diene-1-ols in a chemo-, regio-, and stereoselective manner to give vinylaziridines high yields by means metal-mediated transfer NTs (Ts = p-toluensulfonyl) units from PhI═NTs. The preferential occurs at double bond neighboring hydroxyl end ca. 9:1 ratios that assessed very degree regioselectivity. reaction with silver-based catalysts proceeds stereospecific manner, i.e., initial configuration C═C...
Nitrene transfer: Unsymmetric dienes bearing a terminal hydroxy group can be regio- and stereospecifically converted into vinylaziridines upon nitrene transfer from PhINTs using silver-based catalyst. Stoichiometric mixtures of were employed at low catalyst loadings (0.5 %; see scheme). The method has been applied to the synthesis (±)-sphingosine gave good yields in three-step procedure. Ts=4-toluenesulfonyl. Detailed facts importance specialist readers are published as "Supporting...
Lactimidomycin (1) was described in the literature as an exquisitely potent cell migration inhibitor. Encouraged by this claim, we developed a concise and scalable synthesis of bipartite glutarimide-macrolide antibiotic, which relies on power ring-closing alkyne metathesis (RCAM) for formation unusually strained 12-membered head group. Subsequent deliberate digression from successful path to 1 also brought sister compound isomigrastatin (2) well series non-natural analogues these macrolides...
Abstract A concise and largely catalysis‐based approach to the potent algal toxin polycavernoside ( 1 ) is described that intercepts a late‐stage intermediate of previous total synthesis; from there on, this challenging target can be reached in small number steps. Key success was sequence molybdenum‐catalyzed ring‐closing alkyne metathesis (RCAM) reaction forge macrocyclic frame, followed by gold‐catalyzed strictly regioselective transannular hydroalkoxylation resulting cycloalkyne allows...
Bicyclic amines are important motifs for the preparation of bioactive materials. These species have well-defined exit vectors that enable accurate disposition substituents toward specific areas chemical space. Of all possible skeletons, 2-azabicyclo[3.2.0]heptane framework is virtually absent from MedChem libraries due to a paucity synthetic methods its preparation. Here, we report modular strategy utilizes nitroarenes as flat and easy-to-functionalize feedstocks assembly these sp3-rich...
Ortho-phenylenediamines are aromatic molecules featuring two vicinal N-substituents with strong structural relevance to the development of bioactive materials. These derivatives currently prepared from ortho-halogenated nitrobenzenes via multistep synthetic sequences. Here, we report a conceptually different approach where and amines can be directly converted into ortho-phenylenediamines without need for ortho-halogenation following stepwise manipulation. This strategy occurs under simple...
A general and efficient protocol for the enantioselective synthesis of sphingosine, phythosphingosine, 4-substituted derivatives was established. These compounds were obtained from a common intermediate prepared butadiene monoepoxide by synthetic sequence involving allylic substitution, cross-metathesis, dihydroxylation.
Due to the relevant biological role of sphingosines, ceramides and glycosyl ceramides, increasing demand these compounds for evaluations, developing methods targeting sphingosine phytosphingosine derivatives have attracted interest researchers. The review initially presents structural features compounds, presenting different types nomenclature phytosphingosines, more properties, as well biochemical synthesis. synthetic procedures using products chiral pool, mainly carbohydrates serine...
Abstract Jaspine B and its C‐2 and/or C3 epimers have been enantioselectively prepared from butadiene monoepoxide through a synthetic procedure consisting of allylic amination by palladium‐catalyzed dynamic kinetic asymmetric transformation, cross metathesis, stereoselective dihydroxylation as key steps.
An asymmetric sulfur ylide reaction was employed to prepare an epoxide intermediate in a convergent manner. This efficiently transformed into D-erythro-sphingosine.
Nitrentransfer: Unsymmetrische Diene mit einer endständigen Hydroxygruppe können durch Nitrentransfer von PhINTs in Gegenwart eines Silberkatalysators regio- und stereospezifisch Vinylaziridine umgewandelt werden. Dazu wurden äquimolare Gemische aus Dien sowie nur 0.5 % Katalysator eingesetzt (siehe Schema). Mit dieser Methode war (±)-Sphingosin drei Stufen guten Ausbeuten zugänglich. Ts=4-Toluolsulfonyl. Detailed facts of importance to specialist readers are published as ”Supporting...
Herein, we present a novel C(sp3)–C(sp3) bond-forming protocol via the reductive coupling of abundant tertiary amides with organozinc reagents prepared in situ from their corresponding alkyl halides. Using multistep fully automated flow protocol, this reaction could be used for both library synthesis and target molecule on gram-scale starting bench-stable reagents. Additionally, excellent chemoselectivity functional group tolerance make it ideal late-stage diversification druglike molecules.
Resolvins D3 and E1 are important signaling molecules in the resolution of inflammation. Here, we report a convergent flexible strategy to prepare these natural products using Hiyama–Denmark coupling five- six-membered cyclic alkenylsiloxanes connect three resolvin fragments, control stereochemistry product (Z)-alkenes. The modular nature this approach enables synthesis novel hybrids, opening up opportunities for more-extensive investigations biology.
Abstract Human spermine oxidase (hSMOX) plays a central role in polyamine catabolism. Due to its association with several pathological processes, including inflammation and cancer, hSMOX has garnered interest as possible therapeutic target. Therefore, determination of the structure is an important step enable drug discovery validate Using insights from hydrogen/deuterium exchange mass spectrometry (HDX-MS), we engineered construct obtain first crystal bound known inhibitor MDL72527 at 2.4 Å...
A formal enantioselective synthesis of nectrisine, a potent α-glucosidase inhibitor, was carried out starting from butadiene monoepoxide through synthetic sequence involving allylic substitution, cross-metathesis, dihydroxylation, and cyclization.