title: Asymmetric synthesis of vicinal amino alcohols: xestoaminol C, sphinganine and sphingosine.
abstract: The highly diastereoselective anti-aminohydroxylation of alpha,beta-unsaturated esters, via conjugate addition of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide and subsequent in situ enolate oxidation with (+)-(camphorsulfonyl)oxaziridine, has been used as the key step in the asymmetric synthesis of N,O-diacetyl xestoaminol C (41% yield over 8 steps), N,O,O-triacetyl sphinganine (30% yield over 8 steps) and N,O,O-triacetyl sphingosine (30% yield over 7 steps).
authors.affiliation: Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, UKOX1 3TA.
authors.forename: Elin
authors.initials: E
authors.lastname: Abraham
authors.forename: Stephen G
authors.initials: SG
authors.lastname: Davies
authors.forename: Nicholas L
authors.initials: NL
authors.lastname: Millican
authors.forename: Rebecca L
authors.initials: RL
authors.lastname: Nicholson
authors.forename: Paul M
authors.initials: PM
authors.lastname: Roberts
authors.forename: Andrew D
authors.initials: AD
authors.lastname: Smith
mesh_terms: D005233:Fatty Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D005233:Fatty Alcohols; C476391:xestoaminol C; D013110:Sphingosine; C005682:safingol