Mimics of L-rhamnose: Analogues of rhamnopyranose containing a constituent alpha-amino acid at the anomeric position. A rhamnopyranose analogue of hydantocidin

Ionic brominative oxidation of 2-amino derivatives of protected heptonolactones derived from L-rhamnose provides a key bicyclic intermediate for the synthesis of analogues of L-rhamnopyranose with spirohydantoins and spirodiketopiperazines at the anomeric position; the same intermediate can be used...

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Bibliographic Details
Main Authors: Estevez, J, Smith, M, Wormald, MR, Besra, G, Brennan, P, Nash, R, Fleet, G
Format: Journal article
Published: 1996
Description
Summary:Ionic brominative oxidation of 2-amino derivatives of protected heptonolactones derived from L-rhamnose provides a key bicyclic intermediate for the synthesis of analogues of L-rhamnopyranose with spirohydantoins and spirodiketopiperazines at the anomeric position; the same intermediate can be used for the synthesis of novel glycopeptides containing a constituent rhamnopyranose amino acid. such materials may allow an approach to new studies of diseases induced by mycobacteria, such as tuberculosis and leprosy.