Enantioselective synthesis of lyxo-(2R,3R,4R)-C18-phytosphingosine using double stereodifferentiation

被引：29

作者：

Martin, C ^{[1
]}

Prünck, W ^{[1
]}

Bortolussi, M ^{[1
]}

Bloch, R ^{[1
]}

机构：

[1] Univ Paris 11, Inst Chim Mol Orsay, CNRS, Lab Carbocycles, F-91405 Orsay, France

来源：

TETRAHEDRON-ASYMMETRY | 2000年 / 11卷 / 07期

关键词：

D O I：

10.1016/S0957-4166(00)00106-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

lyxo-C-18-Phytosphingosine can be synthesized by the cis-dihydroxylation of an (E)-allylic trichloroacetamide obtained by an Overman rearrangement. A double stereodifferentiation using AD-mix-beta and an enantiomerically enriched (S)-allylic trichloroacetamide allowed the first synthesis of lyxo-(2R,3R,4R)-C-18-phytosphingosine with high diastereoselectivity (de = 94%) and excellent enantioselectivity (ee = 93%). This sphingosine was fully characterized by the physical and spectral data of the corresponding tetraacetate. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：1585 / 1592

页数：8

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