title: Dihydroxylation of vinyl sulfones: stereoselective synthesis of (+)- and (-)-febrifugine and halofuginone.
abstract: The asymmetric dihydroxylation of amino-functionalized vinyl sulfone 19 has been used for the 3-step preparation of 3-hydroxylpiperidine 24 in 86% enantiomeric excess. This enantiomerically enriched building block was used then to synthesize the naturally occurring antimalarial alkaloid febrifugine 1 and its antiangiogenic analogue, halofuginone 3.
authors.affiliation: Centre for Synthesis and Chemical Biology, School of Chemistry and Chemical Biology, University College Dublin, Dublin 4, Ireland.
authors.forename: Noel P
authors.initials: NP
authors.lastname: McLaughlin
authors.forename: Paul
authors.initials: P
authors.lastname: Evans
mesh_terms: D002384:Catalysis; D006900:Hydroxylation; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D011799:Quinazolines / Q000138:chemical synthesis* / Q000737:chemistry; D052999:Quinazolinones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry*
chemical_list: D010880:Piperidines; D011799:Quinazolines; D052999:Quinazolinones; D013450:Sulfones; C009873:divinyl sulfone; C001207:febrifugine; C010176:halofuginone