6533b855fe1ef96bd12b080e

RESEARCH PRODUCT

Stereoselective synthesis of the naturally occurring styryllactones (+)-goniofufurone and (+)-cardiobutanolide.

J. Alberto MarcoPurificación RuizMiguel CardaJuan Murga

subject

GlycerolMagnetic Resonance SpectroscopybiologyMolecular StructureStereochemistryChemistryOrganic ChemistryEnantioselective synthesisAnnonaceaeStereoisomerismStereoisomerismbiology.organism_classificationChemical synthesisLactonesEnantiopure drugAldol reaction4-ButyrolactoneOrganic chemistryAldol condensationStereoselectivityGoniothalamus

description

The naturally occurring gamma-lactones (+)-goniofufurone 1 and (+)-cardiobutanolide 2, two pharmacologically active products from Goniothalamus species (Annonaceae), have been synthesized in enantiopure form using l-erythrulose as the chiral starting material. Key steps of these syntheses were a stereoselective anti boron aldol reaction and an asymmetric allylboration.

10.1021/jo0483116https://pubmed.ncbi.nlm.nih.gov/15651827