Publication

Use of sultines in the asymmetric synthesis of polypropionate antibiotics

Publications associées (32)

Isocyanoacetates as Synthetic Platform Towards Natural Products and Biologically Relevant Scaffolds

My PhD work started with the development of a racemic access to trigonoliimine B, an hexacyclic alkaloid isolated in 2010. After having explored different strategies, we reported a 7-step synthesis of this natural product. This synthesis features a challen ...

EPFL2014

From Racemic to Enantioselective Total Synthesis of Trigonoliimines via Development of an Organocatalytic Enantioselective Michael Addition of α-Aryl-α-isocyanoacetate to Vinyl Phenyl Selenone

Qian Wang, Thomas Bertrand Pascal Marie Buyck, Jieping Zhu

Trigonoliimines are hexacyclic bisindole alkaloids isolated recently by Hao and co-workers. A synthesis of (±)-trigonoliimine B was accomplished in seven steps from simple starting materials featuring the Bischler-Napieralski reaction for closing the seven ...

Schweizerische Chemische Gesellschaft2014

Catalytic Enantioselective Michael Addition of α-Aryl-α-Isocyanoacetates to Vinyl Selenone: Synthesis of α,α-Disubstituted α-Amino Acids and (+)- and (−)-Trigonoliimine A

Qian Wang, Thomas Bertrand Pascal Marie Buyck, Jieping Zhu

Be like Mike: The title reaction in the presence of the catalyst 1 afforded Michael adducts in excellent yields and enantioselectivities. The adducts were readily converted into alpha,alpha’-disubstituted alpha-amino acids. The enantioselective total synth ...

Wiley-Blackwell2013

Catalytic Formal Homo-Nazarov Reaction and Other Cyclizations of Cyclopropanes : from Methodology to Total Synthesis

Filippo De Simone

The increasing progress in medicinal chemistry and chemical biology requires more versatile synthetic strategies for the generation of libraries of active compounds and theirs analogues. A wide range of biologically active natural and synthetic compounds c ...

EPFL2012

Pd(0)-Catalyzed Oxy- and Aminoalkynylation of Olefins for the Synthesis of Tetrahydrofurans and Pyrrolidines

Jérôme Waser, Stefano Nicolai

The first Pd(0)-catalyzed intramolecular oxy- and aminoalkynylation of nonactivated olefins is reported. The reaction gives access to important tetrahydrofuran and pyrrolidine heterocycles with high diastereoselectivity. The unique synthetic potential of a ...

American Chemical Society2011

Formal Homo-Nazarov and Other Cyclization Reactions of Activated Cyclopropanes

Jérôme Waser, Filippo De Simone, Tanguy Jean Daniel Saget, Fides Benfatti

The Nazarov cyclization of divinyl ketones gives access to cyclopentenones. Replacing one of the vinyl groups by a cyclopropane leads to a formal homo-Nazarov process for the synthesis of cyclohexenones. In contrast to the Nazarov reaction, the cyclization ...

2011

BCl3-Mediated Ene Reaction of Sulfur Dioxide and Unfunctionalized Alkenes

Pierre Vogel, Dean Markovic, Chandra Mouleeswara Rao Volla

The first ene reactions of SO2 and unfunctionalized alkenes are reported. Calculations suggest that the endergonic ene reactions of SO2 with alkenes can be used to generate beta,gamma-unsaturated sulfinyl and sulfonyl compounds. Indeed, in the presence of ...

2010

New developments in iron-catalyzed carbon-carbon bond forming reactions

Chandra Mouleeswara Rao Volla

The goal of this thesis is to develop new carbon-carbon bond forming reactions using inexpensive and simple coupling partners like aryl halides (pseudohalides), sulfonyl derivatives, Grignard reagents, alkenes and alkynes with metal catalysis, preferably u ...

EPFL2009

Ligandless Iron-Catalyzed Desulfinylative C-C Allylation Reactions using Grignard Reagents and Alk-2-enesulfonyl Chlorides

Pierre Vogel, Dean Markovic, Chandra Mouleeswara Rao Volla

Alk-2-enesulfonyl chlorides 1-4 were synthesized by the BCl3-promoted ene reaction of alkenes with SO2. These sulfonyl chlorides were then used as electrophilic partners in iron-catalyzed desulfinylative cross-coupling reactions with different Grignard rea ...

2009

Total asymmetric synthesis of glycomimetics and polypropionates of biological interest

Pierre Vogel

Using readily available chiral auxiliaries such as (+)- and (-)-camphanic acid, (R,R)- and (S,S)-tartaric acid derivatives (e.g. RADO(R)-COCl, SADO(R)-COCl) efficient diastereoselective syntheses of rare sugars and glycomimetics have been developed. They e ...

2008

Investigations of Diels-Alder reactions in ionic liquids

Ana Vidis

Room temperature ionic liquids comprise an unique class of solvent composed of organic and inorganic-based ions that are molten under ambient conditions. They are characterised by high solvent polarity and low vapour pressure, and can be tailored to have s ...

EPFL2007

Palladium-Catalyzed Desulfitative Mizoroki-Heck Coupling Reactions of Sulfonyl Chlorides with Olefins in a Nitrile-functionalized Ionic Liquid

Pierre Vogel, Paul Joseph Dyson, Dongbin Zhao, Zhaofu Fei, Chandra Mouleeswara Rao Volla

Aryl and alkenyl sulfonyl chlorides can be used in Heck-Mizoroki-type couplings with mono- and disubstituted olefins in a nitrile-functionalized ionic liquid, viz. [C3CNpy][Tf2N]. Advantages over previously reported methods include: (1) use of a cheap cat ...

2006