High-pressure hetero-Diels-Alder route to (+/-)-6,6,6-trifluoro-beta-C-naphthyl glycosides.
The first de novo synthesis of a beta-C-naphthyl glycoside displaying a convenient functionality for subsequent transformations into complex C-aryl glycosides is reported. The synthesis of this (+/-)-beta-C-1,5-dibenzyloxynaphthyl 6,6,6-trifluoro-3-amino glycoside relies on a hyperbaric HDA reaction involving a new 2-vinylnaphthalenic dienophile.
Maingot
Lucie
L
UCO2M UMR 6011 CNRS & FR 2575, Universite du Maine, 72085 Le Mans, France.
Leconte
Stéphane
S
Chataigner
Isabelle
I
Martel
Arnaud
A
Dujardin
Gilles
G
D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D006027:Glycosides; D006845:Hydrocarbons, Fluorinated; D009281:Naphthalenes