title: Regioselective and stereospecific amination of iridoids: conversion of aucubin into aminoside antibiotic analogues.
abstract: Treatment of aucubin (1) with tert-butyldimethylsilyl chloride under alkaline conditions permitted regioselective silylation of either the primary hydroxyl groups at C-9 and C-6' or both primary hydroxyl groups and the secondary allylic hydroxyl group at C-6. Acetylation with acetic anhydride, followed by selective removal of the silyl groups and Mitsunobu reaction involving phthalimide as nitrogen donor, gave a stereospecific entry to aminoside antibiotic analogues: 10,6'-diamino-10,6'-dideoxyaucubin (16) and (6R)-6,10,6'-triamino-6,10,6'-trideoxyaucubin (17).
authors.affiliation: Laboratoire de Pharmacognosie, UMR/CNRS 8638, Faculté des Sciences Pharmaceutiques et Biologiques de l'Université René Descartes, 4 Avenue de l'Observatoire, F-75006 Paris, France.
authors.forename: Vokatsoa Christian
authors.initials: VC
authors.lastname: Rakotondramasy
authors.forename: Raphaël
authors.initials: R
authors.lastname: Laschiazza
authors.forename: Marylin
authors.initials: M
authors.lastname: Lecsö-Bornet
authors.forename: Michel
authors.initials: M
authors.lastname: Koch
authors.forename: François
authors.initials: F
authors.lastname: Tillequin
authors.forename: Brigitte
authors.initials: B
authors.lastname: Deguin
mesh_terms: D000586:Amination; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects*; D005960:Glucosides / Q000737:chemistry*; D057888:Iridoid Glucosides; D039823:Iridoids / Q000737:chemistry*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000900:Anti-Bacterial Agents; D005960:Glucosides; D057888:Iridoid Glucosides; D039823:Iridoids; C006650:aucubin