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Enantiospecific, diastereoselective synthesis of Aspidosperma alkaloid analogues from secologanin
β Scribed by Richard T Brown; Mythily Kandasamy
- Publisher
- Elsevier Science
- Year
- 2000
- Tongue
- French
- Weight
- 111 KB
- Volume
- 41
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
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-azepine.
π SIMILAR VOLUMES
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.
^)-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