0000000001309255

AUTHOR

Sandra Hofmann

showing 4 related works from this author

Synthesis of Optically Active N-(4-Hydroxynon-2-enyl)pyrrolidines: Key Building Blocks in the Total Synthesis of Streptomyces coelicolor Butanolide 5…

2021

AbstractStarting from 5-methylhexanal and (S)-configured N-propargylprolinol ethers, coupling delivered N-(4-hydroxynon-2-ynyl)prolinol derivatives as mixtures of C4 diastereomers. Resolution of the epimers succeeded after introduction of an (R)-mandelic ester derivative and subsequent HPLC separation. Alternatively, suitable oxidation gave the corresponding alkynyl ketone. Midland reagent controlled diastereoselective reduction afforded a defined configured propargyl alcohol with high selectivity. LiAlH4 reduction and Mosher analyses of the allyl alcohols enabled structure elucidation. The suitably protected products are used as key intermediates in enantioselective Streptomyces γ-butyrola…

chemistry.chemical_classificationKetonebiologyStereochemistryOrganic ChemistryStreptomyces coelicolorEnantioselective synthesisDiastereomerTotal synthesisPropargyl alcoholbiology.organism_classificationCatalysisProlinolchemistry.chemical_compoundchemistryEpimerSynthesis
researchProduct

Synthesis of (+) and (‐)‐Streptomyces coelicolor Butanolide 5 (SCB‐5)

2021

540 Chemistry and allied sciencesbiologyChemistryStereochemistry540 ChemieOrganic ChemistryStreptomyces coelicolorPhysical and Theoretical Chemistrybiology.organism_classificationEuropean Journal of Organic Chemistry
researchProduct

CCDC 2076144: Experimental Crystal Structure Determination

2021

Related Article: Jonas Donges, Sandra Hofmann, Moritz Brüggemann, Andrea Frank, Dieter Schollmeyer, Udo Nubbemeyer|2021|Eur.J.Org.Chem.|2021|3345|doi:10.1002/ejoc.202100497

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters(3S4S5S)-4-((R)-1-((t-butyl(dimethyl)silyl)oxy)-5-methylhexyl)-5-(iodomethyl)-3-((E)-phenethenyl)dihydrofuran-2(3H)-oneExperimental 3D Coordinates
researchProduct

CCDC 2076145: Experimental Crystal Structure Determination

2021

Related Article: Jonas Donges, Sandra Hofmann, Moritz Brüggemann, Andrea Frank, Dieter Schollmeyer, Udo Nubbemeyer|2021|Eur.J.Org.Chem.|2021|3345|doi:10.1002/ejoc.202100497

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters(3R4R5R)-4-((S)-1-((t-butyl(dimethyl)silyl)oxy)-5-methylhexyl)-5-(iodomethyl)-3-((E)-phenethenyl)-dihydrofuran-2(3H)-oneExperimental 3D Coordinates
researchProduct