Asymmetric synthesis of N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine, jaspine B (pachastrissamine), 2-epi-jaspine B, and deoxoprosophylline via lithium amide conjugate addition

被引：102

作者：

Abraham, Elin ^{[1
]}

Brock, E. Anne ^{[1
]}

Candela-Lena, Jose I. ^{[1
]}

Davies, Stephen G. ^{[1
]}

Georgiou, Matthew ^{[1
]}

Nicholson, Rebecca L. ^{[1
]}

Perkins, James H. ^{[1
]}

Roberts, Paul M. ^{[1
]}

Russell, Angela J. ^{[1
]}

Sanchez-Fernandez, Elena M. ^{[1
]}

Scott, Philip M. ^{[1
]}

Smith, Andrew D. ^{[1
]}

Thomson, James E. ^{[1
]}

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England

来源：

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

关键词：

D O I：

10.1039/b801671b

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 (E)-gamma-tri-iso-propylsilyloxy-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,O,O-tetra-acetyl D-lyxo-phytosphingosine (20% yield over 7 steps), the anhydrophytosphingosine jaspine B (10% yield over 9 steps), 2-epi-jaspine B (14% yield over 9 steps), and the Prosopis alkaloid deoxoprosophylline (26% yield over 7 steps).

引用

页码：1665 / 1673

页数：9

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