Synthesis of vinca alakaloids and related compounds 98. Oxidation with dimethyldioxirane of compounds containing the aspidospermane and quebrachamine ring system. A simple synthesis of (7S,20S)-(+)-rhazidigenine and (2R,7S,20S)-(+)-rhazidine

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....

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Published inJournal of heterocyclic chemistry Vol. 39; no. 4; pp. 767 - 771
Main Authors Eles, J, Kalaus, G, Levai, A, Greiner, Kajtar-Peredy, M, Szabo, P, Szabo, L, Szantay, C
Format Journal Article
LanguageEnglish
Published HOBOKEN Wiley 01.07.2002
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SEEDS
TABERSONINE
PLANTS
INDOLE DERIVATIVES
ALKALOIDS
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Summary: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.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.5570390423