Asymmetric synthesis of vicinal amino alcohols: xestoaminol C, sphinganine and sphingosine?

Organic & Biomolecular Chemistry Pub Date: 2008-03-19 DOI: 10.1039/B801357H

Abstract

The highly diastereoselective anti-aminohydroxylation of α,β-unsaturated esters, viaconjugate addition of lithium (S)-N-benzyl-N-(α-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).

Graphical abstract: Asymmetric synthesis of vicinal amino alcohols: xestoaminol C, sphinganine and sphingosine
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