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

被引：93

作者：

Abraham, Elin ^{[1
]}

Davies, Stephen G. ^{[1
]}

Millican, Nicholas L. ^{[1
]}

Nicholson, Rebecca L. ^{[1
]}

Roberts, Paul M. ^{[1
]}

Smith, Andrew D. ^{[1
]}

机构：

[1] Univ Oxford, Res Lab, Dept Chem, Oxford, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2008年 / 6卷 / 09期

关键词：

D O I：

10.1039/b801357h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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).

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页码：1655 / 1664

页数：10

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