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 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.