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RESEARCH PRODUCT

(-)-Isosteviol as a Versatile Ex-Chiral-Pool Building Block for Organic Chemistry

Magdalena WeckbeckerChristina LohoelterSiegfried R. Waldvogel

subject

Scaffoldchemistry.chemical_compoundchemistryOrganocatalysisOrganic ChemistrySupramolecular chemistryChemical modificationOrganic chemistryPhysical and Theoretical ChemistryBlock (periodic table)Alternative sweetenerMethyl group

description

(–)-Isosteviol is readily available in large quantities by the acidic treatment of a common alternative sweetener. The two functional groups of (–)-isosteviol are presented on the same side of the ent-beyerane scaffold with a mutual C–C distance of about 7 A. Their unique concave arrangement experiences a strong asymmetric environment due to an adjacent methyl group. Consequently, this building block has found several applications in supramolecular chemistry and organocatalysis. These areas and the chemical modification of this scaffold as well as its biological activity are surveyed.

yearjournalcountryeditionlanguage
2013-06-12European Journal of Organic Chemistry
https://doi.org/10.1002/ejoc.201300447