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Highly functionalized cyclopentanes from meso bicyclic hydrazines. A rapid access to mannosidase inhibitors. | LitMetric
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Highly functionalized cyclopentanes from meso bicyclic hydrazines. A rapid access to mannosidase inhibitors.

C Bournaud D Robic M Bonin L Micouin

J Org Chem

Laboratoire de Chimie Thérapeutique, UMR 8638 associée au CNRS et à l'Université René Descartes, Faculté des Sciences Pharmaceutiques et Biologiques, 4 av de l'Observatoire, 75270 Paris Cedex 06, France.

Published: April 2005

A simple diastereoselective access to amino- and hydrazinocyclopentitols is described. The key step involves a cationic rearrangement of a meso bicyclic hydrazine, followed by two successive stereoselective hydroxylations. Both racemic compounds are micromolar alpha-mannosidase (Jack bean) inhibitors.

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 Source
http://dx.doi.org/10.1021/jo047778dDOI Listing

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