Petasis-mediated exo-iminoglycals synthesis from glyconolactams allows access to unprecedented 1-spirocyclopropyl
Lilou Chopin1, Aurélien Beato1, Dylan Yorga1
1Institut de Chimie des Milieux et Matériaux de Poitiers (IC2MP), Université de Poitiers, CNRS, Equipe "Synthèse Organique", Groupe Glycochimie, F-86073, Poitiers, France.
Abstract:
We report herein the olefination of a set of six N-Boc glyconolactams using Petasis reagent to yield unprecedented exoiminoglycals. In addition, a modified Simmons-Smith cyclopropanation was successfully applied to the D-gluco-configured olefin to furnish the unprecedented 1-spirocyclic deoxynojirimycin which proved to be a poor inhibitor of glycosidases in its unprotected form.
Related Concept Videos
Peptidoglycan Synthesis
Biosynthesis of Polysaccharides
Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)
Preparation of Diols and Pinacol Rearrangement
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.

![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
