Synthesis of vinca alakaloids and realated compounds 98 [1]. Oxidation with dimethyldioxirane of compounds containing the aspidospermane and quebrachamine ring system. A simple synthesis of (7s,20S)-(+)-rhazidigenine and (2R,7S,20S)-(+)-rhazidine

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

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11 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)767-771
Number of pages5
JournalJournal of Heterocyclic Chemistry
Volume39
Issue number4
DOIs
Publication statusPublished - Jan 1 2002

ASJC Scopus subject areas

  • Organic Chemistry

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