Skeletal rearrangement of seven-membered iminosugars: Synthesis of (−)-adenophorine,(−)-1-epi-adenophorine and derivatives and evaluation as glycosidase …

…, J Guillard, S Nakagawa, A Kato, Y Blériot

Index: Mondon, Martine; Lecornue, Frederic; Guillard, Jerome; Nakagawa, Shinpei; Kato, Atsushi; Bleriot, Yves Bioorganic and Medicinal Chemistry, 2013 ,  vol. 21,  # 16  p. 4803 - 4812

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Citation Number: 5

Abstract

Abstract The mirror image of natural product (+)-adenophorine along with its 1-epi-, 1-homo- analogs and other derivatives have been synthesized and evaluated as glycosidase inhibitors. The synthetic strategy is based on the skeletal rearrangement of tetrahydroxylated C-alkyl azepanes obtained via a Staudinger/azaWittig/alkylation sequence starting from a sugar-derived azidolactol. Several organometallic species have been investigated for the ...