A short, diastereoselective synthesis of (t)-dihydrocinchonine (7) and (-l-dihydrocinchonidine (8) from their biogenetic precursor, secologanin (la), and lepidine has been achieved in 28% overall yield.
Stereoselective synthesis of yohimbine alkaloids from secologanin
β Scribed by Brown, Richard T.; Pratt, Simon B.
- Book ID
- 120633043
- Publisher
- The Royal Society of Chemistry
- Year
- 1980
- Tongue
- English
- Weight
- 258 KB
- Volume
- 4
- Category
- Article
- ISSN
- 0022-4936
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Pure enantiomers of two diastereomeric Aspidosperma alkaloid analogues antipodal at the spiro and adjacent centres have been prepared, as kinetic and thermodynamic products, respectively, in a biomimetic sequence via a secodine-like intermediate from a secologanin derivative and Kuehne's indolo-azep
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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.