Synthesis of a 5-Spirocyclopropyl Deoxyrhamnojirimycin as a Constrained Naringinase Inhibitor

Morwenna S. M. Pearson; Richard Plantier-Royon; Jan Szymoniak; Philippe Bertus; Jean-Bernard Behr

doi:10.1055/s-2007-990858

SPECIALTOPIC

Synthesis of a 5-Spirocyclopropyl Deoxyrhamnojirimycin as a Constrained Naringinase Inhibitor

Morwenna S. M. Pearson, Richard Plantier-Royon, Jan Szymoniak, Philippe Bertus*, Jean-Bernard Behr*
Laboratoire ‘Réactions Sélectives et Applications’, Université de Reims Champagne-Ardenne, UMR URCA/CNRS 6519, UFR Sciences, BP 1039, 51687 Reims Cedex 2, France
Fax: +33(3)26913166; e-Mail: jb.behr@univ-reims.fr; e-Mail: philippe.bertus@univ-reims.fr;

Abstract

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Abstract

A spirocyclopropyl analogue of deoxyrhamnojirimycin has been synthesized in 11 steps and 20% overall yield from l-arabinose. The key step of the reaction path involves titanium-mediated aminocyclopropanation of an l-arabinononitrile derivative. Improvements of the standard reaction conditions were investigated. The use of methyltitanium triisopropoxide as the titanium source allowed the reaction to take place at room temperature and afforded the corresponding cyclopropylamine in 80% yield.

Key words

glycosidases - imino sugars - metallacycles - nitriles - spiro compounds - titanium

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References

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