Asymmetric synthesis of vicinal amino alcohols: xestoaminol C, sphinganine and sphingosine.
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).
Abraham
Elin
E
Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, UKOX1 3TA.
Davies
Stephen G
SG
Millican
Nicholas L
NL
Nicholson
Rebecca L
RL
Roberts
Paul M
PM
Smith
Andrew D
AD
D005233:Fatty Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D005233:Fatty Alcohols; C476391:xestoaminol C; D013110:Sphingosine; C005682:safingol