A new diorganozinc-based enantioselective access to truncated D-ribo-phytosphingosine

被引：10

作者：

Ayad, T ^{[1
]}

Génisson, Y ^{[1
]}

Verdu, A ^{[1
]}

Baltas, M ^{[1
]}

Gorrichon, L ^{[1
]}

机构：

[1] Univ Toulouse 3, UMR 5068, LSPCMIB, F-31062 Toulouse, France

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 03期

关键词：

phytosphingosine; diorganozinc reagent; double asymmetric induction;

D O I：

10.1016/S0040-4039(02)02526-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The use of a trans alpha,beta-epoxyaldehyde as a precursor Of D-ribo-phytosphingosines was studied. The highly stereoselective alkylation of the aldehyde with a diorganozinc reagent was ensured through double asymmetric induction. The regioselective opening of the epoxide in turn gives access to an azide from which a C-10 phytosphingosine can be easily prepared. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：579 / 582

页数：4

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