Synthesis of New Enantiopure Poly(hydroxy)aminooxepanes as Building Blocks for Multivalent Carbohydrate Mimetics

L. Bouché, M. Kandziora, H.-U. Reissig – 2014

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.

Titel
Synthesis of New Enantiopure Poly(hydroxy)aminooxepanes as Building Blocks for Multivalent Carbohydrate Mimetics
Verfasser
L. Bouché, M. Kandziora, H.-U. Reissig
Datum
2014
Kennung
10.3762/bjoc.10.17
Zitierweise
Beilstein J. Org. Chem. 2014, 10, 213-223
Art
Text
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