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Issue 9, 2008
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Asymmetric synthesis of vicinal amino alcohols: xestoaminol C, sphinganine and sphingosine

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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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Article information


Submitted
24 Jan 2008
Accepted
20 Feb 2008
First published
19 Mar 2008

Org. Biomol. Chem., 2008,6, 1655-1664
Article type
Paper

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

E. Abraham, S. G. Davies, N. L. Millican, R. L. Nicholson, P. M. Roberts and A. D. Smith, Org. Biomol. Chem., 2008, 6, 1655
DOI: 10.1039/B801357H

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