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Reaction of substituted o-aminobenzyl chlorides with isocyanides in the presence of a weak base (NaHCO3) at room temperature afforded the diversely functionalized 2-aminoindoles in good to excellent yields. A formal [4+1] cycloaddition of the in situ gener ...
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
The total synthesis of pentacyclic monoterpene indole alkaloids is the focus of this thesis.
Total syntheses of (±)-alstilobanine C, (±)-undulifoline and (±)-alstilobanine B, three natural products from the Ulean family of alkaloids, were accomplished. The ...
EPFL2018
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We report in this article a cascade reaction strategy for the synthesis of complex N-heterocyclic compounds with contiguous and tetrasubstituted stereogenic carbons. Under the sequential catalysis of a chiral binol–Ti complex and BF3, cyclopentanone-derive ...
We report herein the first examples of a palladiumcatalyzed enantioselective Cacchi reaction for the synthesis of indoles bearing a chiral C2-aryl axis. In the presence of a catalytic amount of Pd(OAc)2 and (R,R)-QuinoxP* ligand, reaction of N-aryl(alkyl)s ...
Organic chemistry is essential for the development of a modern society and technical progress requires the continuous development of synthetic methodologies Novel, efficient, selective and flexible protocols are employed to access complex frameworks from s ...
The tandem synthesis of benzimidazole and other azoles can be achived by the N-formylation of ortho-substituted anilines followed by a cyclization reaction. However, CO2-based N-formylations with hydrosilane reducing agents are base catalyzed whereas the c ...
If small molecules have led to tremendous progress in curing diseases, new therapeutic agents such as peptides or antibody-drugs conjugates have emerged as a highly promising next generation of pharmaceuticals. As for small molecules, their derivatization ...
N-formylation of amines with CO2 and hydrosilane reducing agents proceeds via fast and complex chemical equilibria, which hinder easy analysis of the reaction pathways. In situ reaction monitoring and kinetic studies reveal that three proposed pathways, vi ...
A catalytic enantioselective method for the synthesis of chiral 1H-isoindoles bearing quaternary stereogenic centers is reported. Powered by readily accessible phosphordiamidite ligands, the presented palladium(0)-catalyzed C-H function-alization uses trif ...