Synthesis of pyrrolizidine alkaloids via 1,3-dipolar cycloaddition involving cyclic nitrones and unsaturated lactones

被引：28
|
作者：
Stecko, Sebastian [1 ]
Jurczak, Margarita [1 ]
Urbanczyk-Lipkowska, Zofia [1 ]
Solecka, Jolanta [2 ]
Chmielewski, Marek [1 ]
机构：
[1] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland
[2] Natl Inst Hyg, PL-00791 Warsaw, Poland
来源：
CARBOHYDRATE RESEARCH | 2008年 / 343卷 / 13期
关键词：
nitrone; necine bases; iminosugars; 1,3-dipolar cycloaddition;
D O I：
10.1016/j.carres.2008.04.029
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
The 1,3-dipolar cycloaddition of cyclic nitrone derived from tartaric acid and (S)-5-hydroxymethyl-2(5H)-furanone leads to a single adduct which was transformed into 2,6-dihydroxyhastanecine via reaction sequence involving reduction of the lactone moiety, glycolic cleavage of the terminal diol, and the N-O hydrogenolysis followed by the intramolecular alkylation of the nitrogen atom. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2215 / 2220
页数：6
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