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

页码：2215 / 2220

页数：6

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