An Efficient One-Step Synthesis of Piperidin-2-yl and Pyrrolidin-2-yl Flavonoid Alkaloids through Phenolic Mannich Reactions

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The first chapter of this thesis describe the development of a general synthesis of ynimines, an under-exploited motif in organic chemistry. In the presence of an inexpensive copper catalyst and 2,2'-biquinoline, reaction of easily accessible O-acyloximes ...

Alkynes are found in a multitude of natural or synthetic bioactive compounds. In addition to the capacity of these chemical motifs to impact the physicochemical properties of a molecule of interest, the well-established reactivity of alkynes makes them ide ...

Bromine radical (Br center dot) has been hypothesized to be a key intermediate of bromate formation during ozonation. Once formed, Br center dot further reacts with ozone to eventually form bromate. However, this reaction competes with the reaction of Br c ...

Nitrogen-containing compounds are an important class of molecules in medicinal chemistry, chemical biology, biochemistry, material sciences or environmental sciences. Organic nitrogen occurs in many forms, ranging from small building blocks such as urea, a ...

This thesis consists in an extensive study about the enantioselective Pictet-Spengler reaction (EPSR) and its application to the total synthesis of monoterpene indole alkaloids (MIAs). The general introduction presents the literature background about this ...

Reactive intermediates formed upon irradiation of chromophoric dissolved organic matter (CDOM) contribute to the degradation of various organic contaminants in surface waters. Besides well-studied "short-lived" photo oxidants, such as triplet state CDOM (3 ...

The development of a titanium(III)-mediated cascade electrocyclisation/rearrangement for the enantioselective total synthesis of indole alkaloids (+)-condyfoline and (-)-tubifoline serve as the basis of the first chapter of this thesis. An introduction wil ...

A single-electron transfer (SET) oxidation of indole or benzo[b]thiophene to a radical cation reverses the intrinsic polarity of these pi-excessive bicyclic heteroarenes. Here we report an oxidative two-carbon homologation of cyclobutanols to cyclohexenone ...

Chiral alkyl amines are omnipresent as bioactive molecules and synthetic intermediates. The catalytic and enantioselective synthesis of alkyl amines from readily accessible precursors is challenging. Here we develop a nickel-catalyzed hydroalkylation metho ...

Urolithin A (UA) is a natural compound produced by gut bacteria from ingested ellagitannins (ETs) and ellagic acid (EA), complex polyphenols abundant in foods such as pomegranate, berries, and nuts. UA was discovered 40 years ago, but only recently has its ...

The increasing interest in the fate of organic contaminants in the aquatic environment requires the elucidation of relevant abiotic transformation processes. These processes often involve the ubiquitous dissolved organic matter (DOM), a complex mixture of ...

Deracemization of racemic chiral compounds is an attractive approach in asymmetric synthesis, but its development has been hindered by energetic and kinetic challenges. Here we describe a catalytic deracemization method for secondary benzylic alcohols whic ...

The art of natural product total synthesis is closely associated with two major determinants: the development/application of novel chemical reactions and the innovation in strategic use of classic organic reactions. While purposely seeking/applying a new s ...

The development of a sequential copper-catalyzed oxy-alkynylation/intramolecular [4+2] cycloaddition of allenes and arenes was investigated at first. This one-pot protocol allowed the construction of complex polycylic architectures with high efficiency fro ...

Amino alcohols, cyclopropanes and nitriles are privileged structural motifs found in the scaffold of natural products and bioactive compounds. In addition, they are versatile building blocks in organic chemistry. The development of new and increasingly eff ...

a-Amino ketones and 1,2-amino alcohols are important structural motifs in organic chemistry, that can be observed in natural products, pharmaceutically and bioactive compounds. For these reasons, they constitute privileged targets for the development of ne ...

the strategy involving the use of functionalized tetrahydro-6H-cycloocta[b]indol-6-one is reported as a key intermediate for synthesis of members of the sarpagine-ajmaline-macroline family of monoterpene indole alkaloids. The desired tricycle was synthesiz ...

Five-membered nitrogen-containing heterocyclic compounds (azoles) belong to potential moieties in complex structures where transformations during ozonation can occur. This study focused on the azole-ozone chemistry of pyrrole, imidazole, and pyrazole as mo ...

This review presents an account of the palladium-catalyzed functionalizations of alkenes and alkynes developed at the Laboratory of Catalysis and Organic Synthesis (LCSO). Starting from the intramolecular oxy- and aminoalkynylation of alkenes, tethered met ...

The thesis describes a simple approach for N-formylation of amines with CO2 and hydrosilane reducing agents, the use of organic salts as N-formylation catalysts, their physical properties required for high catalytic activity and their role in the catalytic ...

An Efficient One-Step Synthesis of Piperidin-2-yl and Pyrrolidin-2-yl Flavonoid Alkaloids through Phenolic Mannich Reactions

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Synthesis and Applications of Ynimines and Enantioselective Total Synthesis of Artatrovirenol A

Hypervalent Iodine: New Reagents and Functionalization of Peptides

Reactivity of Bromine Radical with Dissolved Organic Matter Moieties and Monochloramine: Effect on Bromate Formation during Ozonation

Ring-Opening Reactions of Aminocyclopropanes and Aminocyclobutanes

Catalytic enantioselective Pictet-Spengler reaction of carbonyl compounds: Development and application to the asymmetric total synthesis of indole alkaloids

Photochemical oxidation of phenols and anilines mediated by phenoxyl radicals in aqueous solution

Asymmetric Total Synthesis of Indole Alkaloids (+)-Condyfoline, (-)-Tubifoline, (+)-Dasycarpidone and (+)-Uleine

Two-Carbon Ring Expansion of Cyclobutanols to Cyclohexenones Enabled by Indole Radical Cation Intermediate: Development and Application to a Total Synthesis of Uleine

Chiral Alkyl Amine Synthesis via Catalytic Enantioselective Hydroalkylation of Enecarbamates

Impact of the Natural Compound Urolithin A on Health, Disease, and Aging

Phototransformation of Organic Contaminants in Aquatic Systems: Characterization of Long-Lived Photooxidants Derived from Dissolved Organic Matter

Visible-Light-Driven Catalytic Deracemization of Secondary Alcohols

Natural Product Synthesis Enabled by Domino Processes Incorporating a 1,2-Rearrangement Step

New Vinylation and Alkynylation Strategies with Hypervalent Iodine Reagents and Diazo Compounds

New Strategies for the Functionalization of Alkenes Exploiting Tethering Chemistry and Ring Strain

Palladium Catalysed Intramolecular Carbo-oxygenation of Propargylic Amines to Access 1,2-Amino Alcohols and alpha-Amino Ketones via in situ Tether Formation

Towards the Sarpagine-Ajmaline-Macroline Family of Indole Alkaloids: Enantioselective Synthesis of an N-Demethyl Alstolactone Diastereomer

Reactions of pyrrole, imidazole, and pyrazole with ozone: kinetics and mechanisms

Palladium-Catalyzed Functionalization of Olefins and Alkynes: From Oxyalkynylation to Tethered Dynamic Kinetic Asymmetric Transformations (DYKAT)

Organocatalysts in C-N Bond Forming Reactions of Amines with CO2