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, A. Lévai, István Greiner, M. Kajtár-Peredy, P. Szabó, Lajos Szabó, Csaba Szántay

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10 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
Publication statusPublished - Jul 2002

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Oxidation
Hydrochloric Acid
Isomers
Oxides
Derivatives
rhazidine
quebrachamine
dimethyldioxirane
tabersonine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "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",
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.",
author = "J{\'a}nos {\'E}les and Gy{\"o}rgy Kalaus and A. L{\'e}vai and Istv{\'a}n Greiner and M. Kajt{\'a}r-Peredy and P. Szab{\'o} and Lajos Szab{\'o} and Csaba Sz{\'a}ntay",
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language = "English",
volume = "39",
pages = "767--771",
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TY - JOUR

T1 - 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

AU - Éles, János

AU - Kalaus, György

AU - Lévai, A.

AU - Greiner, István

AU - Kajtár-Peredy, M.

AU - Szabó, P.

AU - Szabó, Lajos

AU - Szántay, Csaba

PY - 2002/7

Y1 - 2002/7

N2 - 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.

AB - 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.

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M3 - Article

VL - 39

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JF - Journal of Heterocyclic Chemistry

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