A5040938443- Crystallization and Solubility Studies
- X-ray Diffraction in Crystallography
- Catalytic Alkyne Reactions
- Crystallography and molecular interactions
- Chemical synthesis and alkaloids
- Catalytic C–H Functionalization Methods
- Oxidative Organic Chemistry Reactions
- Sulfur-Based Synthesis Techniques
- Radical Photochemical Reactions
- Alkaloids: synthesis and pharmacology
- Traditional and Medicinal Uses of Annonaceae
- Axial and Atropisomeric Chirality Synthesis
- Cyclopropane Reaction Mechanisms
- Phytochemicals and Antioxidant Activities
- Synthetic Organic Chemistry Methods
- Peptidase Inhibition and Analysis
- Ubiquitin and proteasome pathways
- African history and culture studies
- Sirtuins and Resveratrol in Medicine
- Advanced Materials and Mechanics
- Asymmetric Synthesis and Catalysis
- Berberine and alkaloids research
- Bioactive natural compounds
- Protein Degradation and Inhibitors
- Catalysis and Hydrodesulfurization Studies
University of Zurich
2021-2024
Institut Català d'Investigació Química
2016-2023
Institute of Science and Technology
2017
Barcelona Institute for Science and Technology
2017
University of Michigan
2016
Abstract Two- or one-electron-mediated difunctionalizations of internal alkenes represent straightforward approaches to assemble molecular complexity by the simultaneous formation two contiguous C sp 3 stereocentres. Although racemic versions have been extensively explored, asymmetric variants, especially those involving open-shell C-centred radical species, are much more limited both in number and scope. Here we describe enantioenriched arylsulfinylamides as all-in-one reagents for...
The total synthesis of lundurines A-C has been accomplished in racemic and enantiopure forms 11-13 12-14 steps, respectively, without protection/deprotection functional groups, by a novel tandem double condensation/Claisen rearrangement, gold(I)-catalyzed alkyne hydroarylation, cyclopropanation via formal [3 + 2] cycloaddition/nitrogen extrusion, remarkable olefin migration through vinylcyclopropane retro-ene/ene reaction that streamlines the endgame.
Chiral gold(I) catalysts have been designed based on a modified JohnPhos ligand with distal C2-2,5-diarylpyrrolidine that creates tight binding cavity. The C2-chiral element is close to where the C–C bond formation takes place in cyclizations of 1,6-enynes. These chiral mononuclear applied for enantioselective 5-exo-dig and 6-endo-dig cyclization different 1,6-enynes as well first total synthesis three members carexane family natural products. Opposite enantioselectivities achieved seemingly...
Catching a break in polyphenol synthesis Chemical is usually rather different from playing with modeling kit. If two large fragments of molecule are not properly oriented, it typically possible to them apart, rotate one, and then paste back together. Yet that precisely the trick Keylor et al. used synthesize plant-derived polyphenols. Resveratrol forms variety dimers, trimers, tetramers. When one central carbon-carbon bond links fragments, weak enough spontaneously reversibly at room...
The total synthesis of seven members the lapidilectine and grandilodine family alkaloids has been accomplished in racemic enantiopure form without protection/deprotection functional groups. two key steps, an 8-endo-dig hydroarylation a 6-exo-trig photoredox cyclization, were catalyzed using gold. A rationale for formation cyclopropane ring lundurines is also provided.
The intermolecular gold(I)-catalyzed reaction between arylalkynes and alkenes leads to cyclobutenes by a [2 + 2] cycloaddition, which takes place stepwise, first formation of cyclopropyl gold(I) carbenes, followed ring expansion. However, 1,3-butadienes are also formed in the case ortho-substituted metathesis-type process. corresponding with aryl-1,3-butadiynes, ethynylogous arylalkynes, exclusively cyclobutenes. A comprehensive mechanism for alkynes is proposed on basis density functional...
Proteolysis Targeting Chimeras (PROTACs) are bifunctional molecules that simultaneously bind an E3 ligase and a protein of interest, inducing degradation the latter via ubiquitin-proteasome system. Here we present development degraders targeting CREB-binding (CBP) E1A-associated (EP300)─two homologous multidomain enzymes crucial for enhancer-mediated transcription. Our PROTAC campaign focused on CPI-1612, reported inhibitor histone acetyltransferase (HAT) domain these two proteins. A novel...
Total syntheses of pyrroloazocine indole alkaloids (lapidilectines, grandilodines, lundurines and tenuisines) are discussed in terms existing retrosynthetic solutions novel reaction discoveries.
This Data Descriptor announces the submission to public repositories of monoterpene indole alkaloid database (MIADB), a cumulative collection 172 tandem mass spectrometry (MS/MS) spectra from multiple research projects conducted in eight natural product chemistry laboratories since 1960s. All data have been annotated and organized promote reuse by community. Being unique these complex products, can be used guide dereplication targeting new related alkaloids within mixtures when applying...
A new generation of chiral gold(I) catalysts based on variations complexes with JohnPhos-type ligands a remote C2-symmetric 2,5-diarylpyrrolidine have been synthesized different substitutions at the top and bottom aryl rings: from replacing phosphine by N-heterocyclic carbene (NHC) to increasing steric hindrance bis- or tris-biphenylphosphine scaffolds, directly attaching C2-chiral pyrrolidine in ortho-position dialkylphenyl phosphine. The tested intramolecular [4+2] cycloaddition...
Abstract The first total synthesis of cannabimovone from Cannabis sativa and anhydrocannabimovone was achieved by means a highly stereoselective gold(I)‐catalyzed cycloisomerization. results led to reassignment the structure anhydrocannabimovone.
Abstract The first total synthesis of cannabimovone from Cannabis sativa and anhydrocannabimovone was achieved by means a highly stereoselective gold(I)‐catalyzed cycloisomerization. results led to reassignment the structure anhydrocannabimovone.
Two- or one-electron mediated alkene aminoarylations represent straightforward approaches to assemble molecular complexity by the simultaneous formation of two contiguous Csp3-Csp2/Csp3-N stereocenters. While racemic versions have been extensively explored, asymmetric variants, especially those involving open-shell C-centered radical species, are much more limited both in number and scope. In this work, we describe enantioenriched arylsulfinylamides as all-in-one reagents for efficient...
Two- or one-electron mediated alkene aminoarylations represent straightforward approaches to assemble molecular complexity by the simultaneous formation of two contiguous Csp3-Csp2/Csp3-N stereocenters. While racemic versions have been extensively explored, asymmetric variants, especially those involving open-shell C-centered radical species, are much more limited both in number and scope. In this work, we describe enantioenriched arylsulfinylamides as all-in-one reagents for efficient...