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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).

Original publication

DOI

10.1039/b801357h

Type

Journal article

Journal

Org Biomol Chem

Publication Date

07/05/2008

Volume

6

Pages

1655 - 1664

Keywords

Fatty Alcohols, Molecular Conformation, Sphingosine, Stereoisomerism