Publications by authors named "Julia Pedroni"

8 Publications

  • Page 1 of 1

Isolation, chemistry, and biology of pyrrolo[1,4]benzodiazepine natural products.

Med Res Rev 2021 Apr 13. Epub 2021 Apr 13.

Latvian Institute of Organic Synthesis, Riga, Latvia.

The isolation of the antitumor antibiotic anthramycin in the 1960s prompted extensive research into pyrrolo[1,4]benzodiazepines (PBD) as potential therapeutics for the treatment of cancers. Since then, nearly 60 PBD natural products have been isolated and evaluated with regard to their biological activity. Synthetic studies and total syntheses have enabled access to PBD analogues, culminating in the development of highly potent anticancer agents. This review provides a summary of the occurrence and biological activity of PBD natural products and covers the strategies employed for their total syntheses.
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http://dx.doi.org/10.1002/med.21803DOI Listing
April 2021

Access to P- and Axially Chiral Biaryl Phosphine Oxides by Enantioselective Cp Ir -Catalyzed C-H Arylations.

Angew Chem Int Ed Engl 2018 Sep 29;57(39):12901-12905. Epub 2018 Aug 29.

Laboratory of Asymmetric Catalysis and Synthesis, EPFL SB ISIC LCSA, BCH 4305, CH-, 1015, Lausanne, Switzerland.

An enantioselective C-H arylation of phosphine oxides with o-quinone diazides catalyzed by an iridium(III) complex bearing an atropchiral cyclopentadienyl (Cp ) ligand and phthaloyl tert-leucine as co-catalyst is reported. The method allows access to a) P-chiral biaryl phosphine oxides, b) atropo-enantioselective construction of sterically demanding biaryl backbones, and also c) selective assembly of axial and P-chiral compounds in excellent yields and diastereo- and enantioselectivities. Enantiospecific reductions provide monodentate chiral phosphorus(III) compounds having structures and biaryl backbones with proven importance as ligands in asymmetric catalysis.
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http://dx.doi.org/10.1002/anie.201807749DOI Listing
September 2018

Enantioselective C-H Functionalization-Addition Sequence Delivers Densely Substituted 3-Azabicyclo[3.1.0]hexanes.

J Am Chem Soc 2017 09 1;139(36):12398-12401. Epub 2017 Sep 1.

Laboratory of Asymmetric Catalysis and Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL) , Lausanne, Switzerland.

An enantioselective C-H functionalization route to perfluoroalkyl-containing 3-azabicyclo[3.1.0]hexanes is disclosed. A modular and bench-stable diazaphospholane ligand enables highly enantioselective Pd(0)-catalyzed cyclopropane C-H functionalization using trifluoroacetimidoyl chlorides as electrophilic partners. In turn, the resulting cyclic ketimine products react smoothly with a broad variety of nucleophiles in one-pot processes enabling the rapid and modular construction of heavily substituted pyrrolidines.
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http://dx.doi.org/10.1021/jacs.7b07024DOI Listing
September 2017

2-(Trifluoromethyl)indoles via Pd(0)-Catalyzed C(sp(3))-H Functionalization of Trifluoroacetimidoyl Chlorides.

Org Lett 2016 Apr 7;18(8):1932-5. Epub 2016 Apr 7.

Laboratory of Asymmetric Catalysis and Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne , EPFL SB ISIC LCSA, BCH 4305, CH-1015 Lausanne, Switzerland.

Perfluoroalkylated indoles are valuable compounds in drug discovery. A Pd(0)-catalyzed C(sp(3))-H functionalization enables access to 2-(trifluoromethyl)indoles from trifluoroacetimidoyl chlorides. These are stable compounds, easily obtained from anilines. The cyclization operates with catalyst loadings as low as 1 mol % and accommodates a variety of substituents.
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http://dx.doi.org/10.1021/acs.orglett.6b00795DOI Listing
April 2016

TADDOL-based phosphorus(III)-ligands in enantioselective Pd(0)-catalysed C-H functionalisations.

Chem Commun (Camb) 2015 Dec;51(100):17647-57

Laboratory of Asymmetric Catalysis and Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSA, BCH 4305, CH-1015 Lausanne, Switzerland.

Monodentate TADDOL-derived phosphoramidites and phosphonites are versatile chiral ligands for enantioselective Pd(0)-catalysed C-H functionalisations. They enable highly selective cyclisations to access a wide range of chiral carbo- and heterocycles. The high attractiveness of this ligand class consists in their modular structure, allowing for a quick assembly of a library with variable steric properties. Asymmetric C-H functionalisation methods utilising catalytic systems based on Pd(0) complexes and TADDOL-type ligands are presented and aspects of selectivity are discussed.
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http://dx.doi.org/10.1039/c5cc07929bDOI Listing
December 2015

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

Angew Chem Int Ed Engl 2015 Sep 12;54(40):11826-9. Epub 2015 Aug 12.

Laboratory of Asymmetric Catalysis and Synthesis, EPFL SB ISIC LCSA, BCH 4305, 1015 Lausanne (Switzerland) http://isic.epfl.ch/lcsa.

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 approach which employs a palladium(0)-catalyzed C-H functionalization of an achiral cyclopropane to close the pyrrolidine ring in an enantioselective manner. In contrast to aryl-aryl couplings, palladium(0)-catalyzed C-H functionalizations involving the formation of C(sp(3) )-C(sp(3) ) bonds of saturated heterocycles are very scarce. The presented strategy yields cyclopropane-fused γ-lactams from chloroacetamide substrates. A bulky Taddol phosphonite ligand in combination with adamantane-1-carboxylic acid as a cocatalyst provides the γ-lactams in excellent yields and enantioselectivities.
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http://dx.doi.org/10.1002/anie.201505916DOI Listing
September 2015

Access to β-lactams by enantioselective palladium(0)-catalyzed C(sp3)-H alkylation.

Angew Chem Int Ed Engl 2014 Aug 1;53(34):9064-7. Epub 2014 Jul 1.

Laboratory of Asymmetric Catalysis and Synthesis, EPFL SB ISIC LCSA, BCH 4305, 1015 Lausanne (Switzerland) http://isic.epfl.ch/lcsa.

β-Lactams are very important structural motifs because of their broad biological activities as well as their propensity to engage in ring-opening reactions. Transition-metal-catalyzed C-H functionalizations have emerged as strategy enabling yet uncommon highly efficient disconnections. In contrast to the significant progress of Pd(0)-catalyzed C-H functionalization for aryl-aryl couplings, related reactions involving the formation of saturated C(sp(3))-C(sp(3)) bonds are elusive. Reported here is an asymmetric C-H functionalization approach to β-lactams using readily accessible chloroacetamide substrates. Important aspects of this transformation are challenging C(sp(3))-C(sp(3)) and strain-building reductive eliminations to for the four-membered ring. In general, the β-lactams are formed in excellent yields and enantioselectivities using a bulky taddol phosphoramidite ligand in combination with adamantyl carboxylic acid as cocatalyst.
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http://dx.doi.org/10.1002/anie.201405508DOI Listing
August 2014

Development of an improved rhodium catalyst for z-selective anti-markovnikov addition of carboxylic acids to terminal alkynes.

Chemistry 2013 Sep 22;19(36):12067-76. Epub 2013 Jul 22.

Leibniz-Institut für Katalyse e.V. Albert-Einstein-Strasse 29a, 18059 Rostock (Germany).

To develop more active catalysts for the rhodium-catalyzed addition of carboxylic acids to terminal alkynes furnishing anti-Markovnikov Z enol esters, a thorough study of the rhodium complexes involved was performed. A number of rhodium complexes were characterized by NMR, ESI-MS, and X-ray analysis and applied as catalysts for the title reaction. The systematic investigations revealed that the presence of chloride ions decreased the catalyst activity. Conversely, generating and applying a mixture of two rhodium species, namely, [Rh(DPPMP)2][H(benzoate)2] (DPPMP=diphenylphosphinomethylpyridine) and [{Rh(COD)(μ2-benzoate)}2], provided a significantly more active catalyst. Furthermore, the addition of a catalytic amount of base (Cs2CO3) had an additional accelerating effect. This higher catalyst activity allowed the reaction time to be reduced from 16 to 1-4 h while maintaining high selectivity. Studies on the substrate scope revealed that the new catalysts have greater functional-group compatibility.
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http://dx.doi.org/10.1002/chem.201300160DOI Listing
September 2013