A sort synthesis of polyhydroxylated pyrrolizidines via sequential 1,3-dipolar cycloaddition and reductive amination

被引：10

作者：

Gkizis, Petros ^{[1
]}

Argyropoulos, Nikolaos G. ^{[1
]}

Coutouli-Argyropoulou, Evdoxia ^{[1
]}

机构：

[1] Aristotle Univ Thessaloniki, Dept Chem, Organ Chem Lab, Thessaloniki 54124, Greece

来源：

TETRAHEDRON | 2013年 / 69卷 / 42期

关键词：

Pyrrolizidines; Reductive amination; 1,3-Dipolar cycloaddition; Nitrones; Azasugars; 1ST ASYMMETRIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; ENANTIOSPECIFIC SYNTHESIS; CYCLIC NITRONES; GLYCOSIDASE INHIBITORS; HYACINTHACINE A(1); NATURAL OCCURRENCE; ALKALOIDS; AUSTRALINE; STRATEGY;

D O I：

10.1016/j.tet.2013.07.098

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Polyhydroxylated pyrrolizidines bearing a methyl group at C-5 have been synthesized by 1,3-dipolar cycloaddition of five membered cyclic nitrones with methyl vinyl ketone followed by a N-O reductive cleavage and in situ intramolecular reductive amination. The stereochemistry of the obtained compounds is examined in relation to the reactions mechanism. (c) 2013 Elsevier Ltd. All rights reserved.

引用

页码：8921 / 8928

页数：8

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