Regioselective and stereospecific amination of iridoids: conversion of aucubin into aminoside antibiotic analogues.
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).
Rakotondramasy
Vokatsoa Christian
VC
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.
Laschiazza
Raphaël
R
Lecsö-Bornet
Marylin
M
Koch
Michel
M
Tillequin
François
F
Deguin
Brigitte
B
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
D000900:Anti-Bacterial Agents; D005960:Glucosides; D057888:Iridoid Glucosides; D039823:Iridoids; C006650:aucubin