Synthesis of the Potential Mannosidase Inhibitor via 1,3-Dipolar Cycloaddition Involving Cyclic Nitrone and Unsaturated Chiral γ-Lactone

被引：0

作者：

Stecko, S. ^{[1
]}

Pasniczek, K. ^{[1
]}

Jurczak, M. ^{[1
]}

Solecka, J. ^{[2
]}

Chmielewski, M. ^{[1
]}

机构：

[1] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland

[2] Natl Inst Hyg, PL-00791 Warsaw, Poland

来源：

POLISH JOURNAL OF CHEMISTRY | 2009年 / 83卷 / 02期

关键词：

nitrone; iminosugars; 1,3-dipolar cycloaddition; DOUBLE ASYMMETRIC INDUCTION; REGIOSELECTIVE OXIDATION; NATURAL OCCURRENCE; ALKALOIDS; ACID; DFT;

D O I：

暂无

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The 1,3-dipolar cycloaddition of cyclic nitrone derived from tartaric acid with (S)-5-hydroxymethyl-2(5H)-furanone leads to a single adduct which was transformed into 1,2,6,7-tetrahydroxy-2-hydroxymethyl-indolizidine via reaction sequence involving protection of the hydroxymethyl group, reduction of the lactone moiety, protection of the resulting diol, and the N-O hydrogenolysis followed by the intramolecular alkylation of the nitrogen atom.

引用

页码：237 / 243

页数：7

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