6533b859fe1ef96bd12b8402

RESEARCH PRODUCT

Synthesis of novel functionalized cispentacins through C–C oxidative cleavage of diendo-norbornene β-amino acid

Maria CherepanovaReijo SillanpääLoránd KissFerenc FülöpFerenc Fülöp

subject

chemistry.chemical_classificationDouble bondStereochemistryGeneral Chemical EngineeringGeneral ChemistryOxidative phosphorylationCleavage (embryo)Amino acidStereocenterchemistry.chemical_compoundchemistryDihydroxylationWittig reactionta116Norbornene

description

Difunctionalized cispentacin derivatives with two new stereogenic centres have been synthesized from a diendo-norbornene β-amino acid in a stereocontrolled route, involving C–C double bond functionalization by dihydroxylation, followed by oxidative ring cleavage and transformation of the dialdehyde intermediates through a Wittig reaction.

https://doi.org/10.1039/c3ra41963k