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Start Over Author "Lajos Dr Szabo" Journal journal of heterocyclic chemistry
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1. Synthesis of vinca alakaloids and realated compounds98. Oxidation with dimethyldioxirane of compounds containing the aspidospermane and quebrachamine ring system. A simple synthesis of (7S,20S)-(+)-rhazidigenine and (2R,7S,20S)-(+)-rhazidine

Author

Mária Kajtár-Peredy, György Kalaus, Lajos Dr Szabo, Csaba Szántay, Pál Szabó, Albert Lévai, István Greiner, and János Éles

Subjects
Quebrachamine, chemistry.chemical_compound, Vinca, chemistry, biology, Organic Chemistry, Organic chemistry, Hydrochloric acid, Dimethyldioxirane, biology.organism_classification, Ring (chemistry), Derivative (chemistry), System a
Abstract

The oxidation of (-)-tabersonine (1) with dimethyldioxirane (DMD) in neutral and acidic medium gave 16-hydroxytabersonine-N-oxide (3) and the didehydrovincamine isomers 4 and 5, respectively. (+)-14,15-Didehydro-quebrachamine (7) furnished the hydroxyindolenine 9, and the pentacyclic derivative 11. (+)-Quebrachamine (8) and DMD in neutral medium gave (7S,20S)-(+)-rhazidigenine (12) which was converted to (2R,7S,20S)-(+)-rhazidine (13b) with hydrochloric acid.

Published
2002
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