Organocatalyzed synthesis of (-)-4-epi-fagomine and the corresponding pipecolic acids

被引：10

作者：

Marjanovic, Jasna ^{[2
]}

Ferjancic, Zorana ^{[1
]}

Saicic, Radomir N. ^{[1
]}

机构：

[1] Univ Belgrade, Fac Chem, Studentski Trg 16,POB 51, Belgrade 11158, Serbia

[2] Fac Chem, Innovat Ctr, Belgrade, Serbia

来源：

TETRAHEDRON | 2015年 / 71卷 / 38期

关键词：

Organocatalysis; Iminosugars; Fagomine; Pipecolic acids; Glycolipid storage disorders; LYSOSOMAL ALPHA-GALACTOSIDASE; DE-NOVO SYNTHESIS; GLYCOSIDASE INHIBITORS; ASYMMETRIC INDUCTION; FABRY LYMPHOBLASTS; NATURAL OCCURRENCE; ALDOL REACTIONS; DERIVATIVES; 1-DEOXYGALACTONOJIRIMYCIN; MOLECULES;

D O I：

10.1016/j.tet.2015.07.036

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective synthesis of 4-epi-fagomine was accomplished starting from dioxanone and Cbz-protected benyzlamine, in 4 steps, with 18% overall yield. The key feature of this synthetic approach is the tactical combination of reactions: organocatalyzed aldolization/reductive amination, which allows for a quick formation of heterocyclic rings with defined absolute configuration of all stereogenic centers. Two hydroxypipecolic acids and a reduced fagomine analogue were also synthesized. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：6784 / 6789

页数：6

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