6533b7dbfe1ef96bd12708f0

RESEARCH PRODUCT

Model studies on a diastereoselective synthesis of the C(33)–C(37) fragment of Amphotericin B

Ari M. P. KoskinenMaija NissinenKaisa KarisalmiKari Rissanen

subject

chemistry.chemical_classificationChemistryStereochemistryFragment (computer graphics)Organic ChemistryEnantioselective synthesisBiochemistryAldehydeStereocenterBenzaldehydechemistry.chemical_compoundAldol reactionAmphotericin BDrug DiscoverymedicineMoleculemedicine.drug

description

Abstract A new, short and highly diastereoselective synthetic route aiming at the C(33)–C(37) fragment of Amphotericin B has been developed. Studies with a model aldehyde (benzaldehyde) have given very promising results: the desired stereochemistry of all four stereocenters of the target molecule has been achieved with high diastereoselection. The stereochemistry of three key intermediates and the target segment has been confirmed by X-ray crystallography.

https://doi.org/10.1016/s0040-4020(03)00070-x