Hydrolysis of secologanin ethylene acetal at pH 7 resulted in stereoselective aldol cyclisation to a cyclohexene aldehyde, which, on reductive amination and cyclisation with tryptamine aorded (^)-3-iso-19,20dehydro-b-yohimbine, converted into various normal and pseudo isomers of yohimbine.
Synthesis of /±/-yohimbine and /±/-β-yohimbine. A new route to yohimban ring system.
✍ Scribed by Cs. Szántay; L. Tőke; K. Honti
- Publisher
- Elsevier Science
- Year
- 1965
- Tongue
- French
- Weight
- 238 KB
- Volume
- 6
- Category
- Article
- ISSN
- 0040-4039
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📜 SIMILAR VOLUMES
^)-3-Iso-19,20-dehydro-b-yohimbine has been converted into epiallo-yohimbines and, via a novel regioand stereoselective hydration, into the 18R-hydroxy derivative, an analogue of deserpidine. Its 11-methoxy derivative, also prepared from secologanin, is a potential precursor for a reserpine analogue
The l,&addition of nucleophiles to activated butadienes was first demonstrated by Kohler and Butler (1) in the reaction of sodiomalonic ester with methyl B-vinylacrylate(1).
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