Asymmetric synthesis of orthogonally protected (2S,4R)- and (2S,4S)-4-hydroxyornithine
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Asymmetric hydrogenations are among the most practical methods for the synthesis of chiral building blocks at industrial scale. The selective reduction of an oxime to the corresponding chiral hydroxylamine derivative remains a challenging variant because o ...
Pentamethylcyclopentadienyl (Cp*) based transition-metal-catalyzed C-H functionalization has become an important synthetic tool for the construction of molecular complexity from simple starting materials. Despite their high potential, the corresponding asy ...
Chiral auxiliaries and asymmetric catalysis are the workhorses of enantioselective transformations, but they still remain limited in terms of either efficiency or generality. Herein, we present an alternative strategy for controlling the stereoselectivity ...
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 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 ...
Cp*Ir(III) catalyzed C-H functionalization is a growing field, since it provides novel complementary reactivities, but enantioselective C-H functionalization reactions with this metal remain a niche. This thesis investigates CpXIr(III) catalyzed asymmetric ...
A concise synthesis of pharmaceutically useful (R)-tert-butyl N-(2-bromo-9-methyl-6,7,8,9-tetrahydro-5H-pyrido [2,3-b ] indol-6-yl) -N-methylcarbamate building block 11 is described. The racemic intermediate 17 was prepared in a single step from 2-bromo-6- ...
Production of optically pure products can be based on simple unselective synthesis of racemic mixtures combined with a subsequent separation of the enantiomers; however, this approach suffers from a 50% yield limitation which can be overcome by racemizatio ...
Looking for hidden symmetry: The first asymmetric total synthesis of pentacyclic (E)- and (Z)-alstoscholarines is accomplished starting from cyclic meso-anhydride 9. The absolute configuration was set by an organocatalytic desymmetrization of 9. Other key ...
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 ...
