Synthesis of new enantiopure poly(hydroxy)aminooxepanes as building blocks for multivalent carbohydrate mimetics

被引：16

作者：

Bouche, Lea ^{[1
]}

Kandziora, Maja ^{[1
]}

Reissig, Hans-Ulrich ^{[1
]}

机构：

[1] Free Univ Berlin, Inst Chem & Biochem, D-14195 Berlin, Germany

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 10卷

关键词：

aminooxepanes; carbohydrate mimetics; hydrogenolyses; Lewis acid-induced; lithiated allenes; nitrones; 1,2-oxazines; rearrangements; reductions; ENANTIOSPECIFIC TOTAL-SYNTHESIS; ACID PROMOTED REARRANGEMENT; AJMALINE-RELATED ALKALOIDS; RING-CLOSING METATHESIS; NITRONE CYCLOADDITION; AMINO-SUGARS; 1,2-OXAZINES; SEPTANOSIDES; OXEPINES; (-)-RAUMACLINE;

D O I：

10.3762/bjoc.10.17

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New compounds with carbohydrate-similar structure (carbohydrate mimetics) are presented in this article. Starting from enantiopure nitrones and lithiated TMSE-allene we prepared three 1,2-oxazine derivatives which underwent a highly stereoselective Lewis acid-induced rearrangement to give bicyclic products in good yield. Subsequent reductive transformations delivered a library of new poly(hydroxy) aminooxepane derivatives. The crucial final palladium-catalyzed hydrogenolysis of the 1,2-oxazine moiety was optimized resulting in a reasonably efficient approach to a series of new seven-membered carbohydrate mimetics.

引用

页码：213 / 223

页数：11

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