Hydroxylation of yohimbine in superacidic media: one-step access to human metabolites 10 and 11-hydroxyyohimbine.
Two major human metabolites of yohimbine (1), 10- and 11-hydroxyyohimbine (2 and 3), were prepared by direct hydroxylation of 1 under superacidic conditions. In this medium, the four positions of the benzene part of yohimbine were hydroxylated and the corresponding monohydroxylated compounds (2-5) were isolated. The structures of 2-5 were elucidated by spectroscopic methods including 1D and 2D NMR techniques.
Duflos
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A
Centre de Recherche Pierre Fabre, 17 Avenue Jean Moulin, Castres F 81106, France. alain.duflos@pierre-fabre.com
Redoules
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F
Fahy
J
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Jacquesy
J C
JC
Jouannetaud
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MP
D002625:Chemistry, Organic / Q000379:methods; D006801:Humans; D006858:Hydrofluoric Acid; D006900:Hydroxylation; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D015016:Yohimbine / Q000031:analogs & derivatives* / Q000378:metabolism*
C081038:11-hydroxyyohimbine; D015016:Yohimbine; C081037:10-hydroxyyohimbine; D006858:Hydrofluoric Acid