Publications associées à Catalytic Atropenantioselective Heteroannulation between Isocyanoacetates and Alkynyl Ketones: Synthesis of Enantioenriched Axially Chiral 3-Arylpyrroles

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

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 ...

EPFL2023

Indole Alkaloids, Macrocycles and Heterocycles : Interplay between Methodological Development and Total Synthesis

Cyril Piemontesi

An enantioselective total synthesis of (-)-terengganensine A, a heptacyclic monoterpene indole alkaloid, was performed. A short sequence allowed to obtain the enantio-enriched target in good overall yield. The synthesis featured a key asymmetric transfer h ...

EPFL2018

Chiral gamma-Lactams by Enantioselective Palladium(0)-Catalyzed Cyclopropane Functionalizations

Nicolai Cramer, Julia Pedroni

Cyclopropanes fused to pyrrolidines are important structural features found in a number of marketed drugs and development candidates. Typically, their synthesis involves the cyclopropanation of a dihydropyrrole precursor. Reported herein is a complementary ...

Wiley-VCH Verlag GmbH2015

Isocyanoacetates as Synthetic Platform Towards Natural Products and Biologically Relevant Scaffolds

Thomas Bertrand Pascal Marie Buyck

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

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, Jieping Zhu, Thomas Bertrand Pascal Marie Buyck

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

Use of sultines in the asymmetric synthesis of polypropionate antibiotics

Pierre Vogel, Maris Turks, Cotinica Craita, Freddy Fonquerne, Laure Bouchez, Christopher Flowers, Xiaogen Huang

At low temperature and in the presence of an acid catalyst, SO2 adds to 1,3-dienes equilibrating with the corresponding 3,6-dihydro-1,2-oxathiin-2-oxides (sultines). These compounds are unstable above -60 degrees C and equilibrate with the more stable 2,5- ...

De Gruyter2008