0000000001311264

AUTHOR

Natalie Netz

showing 7 related works from this author

One-Pot Synthesis of Pyrrole-2-carboxylates and -carboxamides via an Electrocyclization/Oxidation Sequence

2014

An electrocyclic ring closure is the key step of an efficient one-pot method for the synthesis of pyrrole-2-carboxylates and -carboxamides from chalcones and glycine esters or amides. The 3,4-dihydro-2H-pyrrole intermediates generated in situ are oxidized to the corresponding pyrroles by stoichiometric oxidants or by catalytic copper(II) and air in moderate to high yields. A wide range of functional groups are tolerated, and further combination with an in situ bromination gives access to polyfunctional pyrrole scaffolds.

ProlineOrganic ChemistryOne-pot synthesischemistry.chemical_elementHalogenationEstersStereoisomerismStereoisomerismElectrochemistryRing (chemistry)Combinatorial chemistryCopperCatalysisCatalysischemistry.chemical_compoundchemistryCyclizationElectrochemistryPyrrolesOxidation-ReductionCopperPyrroleThe Journal of Organic Chemistry
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A Modular Formal Total Synthesis of (±)-Cycloclavine

2016

Cycloclavine is a clavine-type Ergot alkaloid noteworthy for its unique pentacyclic skeleton featuring a 3-azabicyclo[3.1.0]hexane substructure. A short convergent route to the racemic alkaloid is described which comprises only eight linear steps and requires only four chromatographic purifications. The two key building blocks can be prepared in high yield from commercially available starting materials. Two consecutive coupling reactions, namely a selective alkylation of a dienolate and a Heck reaction, are the key steps of the reaction sequence.

CycloclavineAlkylationMolecular Structure010405 organic chemistryOrganic ChemistryTotal synthesisStereoisomerismStereoisomerismAlkylationBridged Bicyclo Compounds Heterocyclic010402 general chemistry01 natural sciencesCoupling reactionIndole Alkaloids0104 chemical sciencesHexanechemistry.chemical_compoundchemistryCyclizationHeck reactionYield (chemistry)HexanesOrganic chemistryThe Journal of Organic Chemistry
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Modular De novo Synthesis of Unsymmetrical BODIPY Dyes Possessing Four Different Aryl Substituents

2017

A modular synthesis of unsymmetrical BODIPY dyes based on a [6π]-electrocyclization to construct the two pyrrole rings is presented. The products carry four aryl moieties in positions 1, 3, 5, and 7 which can be freely selected as well as optional substitution in positions 2 and 8. The method employs acetophenones, benzaldehydes as well as glycine nitrile or glycine ethyl ester as the key building blocks.

Nitrile010405 organic chemistryChemistryStereochemistrybusiness.industryArylOrganic ChemistryModular design010402 general chemistry01 natural sciences0104 chemical sciencesDe novo synthesischemistry.chemical_compoundGlycinePhysical and Theoretical ChemistryBODIPYGlycine ethyl esterbusinessPyrroleEuropean Journal of Organic Chemistry
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ChemInform Abstract: One-Pot Synthesis of Pyrrole-2-carboxylates and -carboxamides via an Electrocyclization/Oxidation Sequence.

2015

An electrocyclic ring closure is the key step of an efficient one-pot method for the synthesis of pyrrole-2-carboxylates and -carboxamides from chalcones and glycine esters or amides. The 3,4-dihydro-2H-pyrrole intermediates generated in situ are oxidized to the corresponding pyrroles by stoichiometric oxidants or by catalytic copper(II) and air in moderate to high yields. A wide range of functional groups are tolerated, and further combination with an in situ bromination gives access to polyfunctional pyrrole scaffolds.

chemistry.chemical_compoundChemistryGlycineOne-pot synthesisHalogenationchemistry.chemical_elementOrganic chemistryGeneral MedicineRing (chemistry)CopperStoichiometryPyrroleCatalysisChemInform
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Marine Indole Alkaloids.

2015

Marine indole alkaloids comprise a large and steadily growing group of secondary metabolites. Their diverse biological activities make many compounds of this class attractive starting points for pharmaceutical development. Several marine-derived indoles were found to possess cytotoxic, antineoplastic, antibacterial and antimicrobial activities, in addition to the action on human enzymes and receptors. The newly isolated indole alkaloids of marine origin since the last comprehensive review in 2003 are reported, and biological aspects will be discussed.

540 Chemistry and allied sciencesAquatic Organismscarbolinesprenylated indolesmarine natural productsAntineoplastic AgentsReviewindolesalkaloidsbisindolesdiketopiperazinesIndole AlkaloidsBiological Factorslcsh:Biology (General)Anti-Infective Agents540 ChemieHumansnitrogen heterocycleslcsh:QH301-705.5Marine drugs
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CCDC 1055316: Experimental Crystal Structure Determination

2015

Related Article: Dennis Imbri , Natalie Netz , Murat Kucukdisli , Lisa Marie Kammer , Philipp Jung , Annika Kretzschmann , and Till Opatz|2014|J.Org.Chem.|79|11750|doi:10.1021/jo5021823

Space GroupCrystallographyCrystal SystemCrystal Structure5-(4-Fluorophenyl)-3-(4-methoxyphenyl)-N-(2-methylpropyl)-1H-pyrrole-2-carboxamideCell ParametersExperimental 3D Coordinates
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CCDC 1055315: Experimental Crystal Structure Determination

2015

Related Article: Dennis Imbri , Natalie Netz , Murat Kucukdisli , Lisa Marie Kammer , Philipp Jung , Annika Kretzschmann , and Till Opatz|2014|J.Org.Chem.|79|11750|doi:10.1021/jo5021823

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parametersethyl 5-(4-chlorophenyl)-3-(3-nitrophenyl)-1H-pyrrole-2-carboxylateExperimental 3D Coordinates
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