Synthesis of Novel Iminosugar Derivatives Based on a 2-Azabi­cyclo[4.1.0]heptane Skeleton

Abstract

Iminosugars are good starting points for the development of different kinds of drugs. Many are polyhydroxylated piperidines that behave as biomimetics of their corresponding pyranoses analogues. In the interaction with carbohydrate processing enzymes, selectivity is a crucial issue and the benefits of introducing a cyclopropane bridge in a piperidine structure is demonstrated. The synthesis of novel bicyclic piperidine-based iminosugars using a sulfur ylide cyclopropanation as the key synthetic step is described.

Key words

bicyclic compounds - piperidines - stereoselective synthesis - ylides - iminosugars - cyclopropanation

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