Publications related to Enantioselective Synthesis of Putative Lipiarmycin Aglycon Related to Fidaxomicin/Tiacumicin B

Related publications (18)

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

Asymmetric Cyclopropanation and Epoxidation via a Catalytically Formed Chiral Auxiliary

Jérôme Waser, Mikus Purins

For the enantioselective diversification of a single starting material, a different chiral catalyst is usually required for each transformation. Herein, we extend the concept of catalytically formed chiral auxiliary from hydrogenation to the asymmetric cyc ...

Wiley-VCH Verlag GmbH2022

Chiral Cyclopentadienyl Ligands: Design, Syntheses, and Applications in Asymmetric Catalysis

Ana Garcia Herraiz, Nicolai Cramer, Benoît Daniel Bertrand Audic, Josep Más-Roselló, Aragorn Nathan Laverny

The creation of new chiral ligands capable of providing high stereocontrol in metal-catalyzed reactions is crucial in modern organic synthesis. The production of bioactive molecules as single enantiomers is increasingly required, and asymmetric catalysis w ...

Wiley-VCH Verlag GmbH2021

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

Guillaume Dominique Pisella

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 ...

EPFL2021

Getting the Right Grip? How Understanding Electrophile Selectivity Profiles Could Illuminate Our Understanding of Redox Signaling

Yimon Aye, Lingxi Wang

Recent Advances: Herein, we focus on the first step of this process, electrophile sensing. Electrophile sensing is typically a deceptively simple reaction between the thiol of a protein cysteine, of which there are around 200,000 in the human proteome, and ...

MARY ANN LIEBERT, INC2020

TiCl3-Mediated Synthesis of 2,3,3-Trisubstituted Indolenines: Total Synthesis of (+)-1,2-Dehydroaspidospermidine, (+)-Condyfoline, and (-)-Tubifoline

Jieping Zhu, Qian Wang, Cyril Piemontesi, Bastien Delayre

2,3,3-Trisubstituted indolenine constitutes an integral part of many biologically important monoterpene indole alkaloids. We report herein an unprecedented access to this skeleton by a TiCl3-mediated reductive cyclization of tetrasubstituted alkenes bearin ...

Wiley-VCH Verlag GmbH2020

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

Martin Hulla

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 ...

EPFL2019

Stereoselective synthesis of alkenes via base-metal-catalyzed addition reactions to alkynes and activation of hydrogen peroxide and carbon dioxide by iron complexes

Fedor Zhurkin

Alkene functionality can be found in the majority of natural products, drugs, catalysts and organic materials. Therefore, methods of C-C double bond formation constitute a cornerstone of organic synthesis. Selective formation of either (Z)- or (E)-isomer i ...

EPFL2017

Elucidating the Role of Site-Specific Nitration of alpha-Synuclein in the Pathogenesis of Parkinson's Disease via Protein Semisynthesis and Mutagenesis

Hilal Lashuel, Anass Chiki, Nadine Aït Bouziad, Ritwik Burai

Parkinsons disease (PD) is characterized by the loss of dopaminergic neurons in the substantia nigra and the presence of intraneuronal inclusions consisting of aggregated and post-translationally modified a-synuclein (a-syn). Despite advances in the chemic ...

Amer Chemical Soc2015

Chiral Cyclopentadienyl Rh(III)-Complexes for Asymmetric C-H Functionalizations

Baihua Ye

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 ...

EPFL2015

Chiral Phosphoric Acid-Catalyzed Enantioselective Three- Component Aza-Diels-Alder Reactions of Aminopyrroles and Aminopyrazoles

Jieping Zhu, Thibaut Christian Courant

A highly stereoselective three-component Povarov reaction, catalyzed by (R)- and (S)-BINOL hydrogen phosphate, was achieved for the first time with aminopyrroles and aminopyrazoles as 2-azadiene precursors. A variety of aldehydes, enecarbamates, amino-subs ...

Wiley-Blackwell2014

Enantioselective Total Syntheses of Leuconolam–Leuconoxine–Mersicarpine Group Monoterpene Indole Alkaloids

Jieping Zhu, Qian Wang, Zhengren Xu

A unified strategy allowing enantioselective total syntheses of (−)-mersicarpine, (−)-scholarisine G, (+)-melodinine E, (−)-leuconoxine, and (−)-leuconolam from a common cyclohexenone derivative was reported. The Suzuki−Miyaura reaction was used to couple ...

2013

Total Synthesis of Cyrneine A

Karl Gademann, Cindy Fellay

The tricyclic diterpene cyrneine A featuring a hexatrienal unit was prepared synthetically for the first time by a Heck reaction, a carbene ring expansion, and a reductive carbonylation. The structure of the natural product was assigned by X‐ray crystal an ...

Wiley-VCH Verlag GmbH2012

Enantioselective Synthesis of 4-Hydroxytetrahydropyridine Derivatives by Intramolecular Addition of Tertiary Enamides to Aldehydes

Jieping Zhu, Shuo Tong

Wiley-Blackwell2012

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

Synthesis of aza-C-disaccharides (dideoxyimino-alditols C-linked to monosaccharides) and analogues

Pierre Vogel

The first aza-C-disaccharide (D-azaMan-beta-CHz-(1 -> 6)-D-Man-alpha-OMe) that mimicks alpha-D-Manp-(1 -> 6)-alpha-D-ManOMe was made in 1994 by Johnson and coworkers. Several synthetic approaches to these disaccharide mimetics have been proposed. These are ...

Georg Thieme Verlag2005

Expeditious asymmetric synthesis of a stereoheptad corresponding to the C(19)-C(27)-ansa chain of rifamycins: Formal total synthesis of Rifamycin S

Pierre Vogel, Maris Turks, Xiaogen Huang

In the presence of sulfur dioxide and an acid promoter, (-)-(1E,3Z)-2-methyl-1-((1S)-1-phenyleth- oxy)penta-1,3-dien-3-yl isobutyrate reacts with (Z)-3-(trimethylsilyloxy)-pent-2-ene giving a silyl sulfinate intermediate that undergoes, in the presence of ...

2005

Le réarrangement [1,2] de Wittig : contribution à l'étude de son mécanisme et de ses applications

Frédéric Bailly

The importance of catalysis in chemistry has not to be proved anymore. Be it homogeneous or heterogeneous catalysis, the constant progresses observed in that field proves its obvious interest. The asymmetric homogeneous catalysis is a method of choice to s ...

EPFL2005