Aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methyl-, methyl ester, (2beta,3beta,4beta,5alpha,12beta,19alpha)- → 3',4'-Anhydrovinblastine

HRID 1086978

Reaktionsgleichung

Reaktionsgleichung von HRID 1086978
[CH3:1][CH2:2][C:3]1[C@H:8]2[N:9]3[CH2:11][CH2:12][C:13]4[C:21]5[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=5)[NH:15][C:14]=4[C@@:7]2([C:22]([O:24][CH3:25])=[O:23])[CH2:6][C@@H:5]([CH2:10]3)[CH:4]=1.[CH3:26][CH2:27][C:28]12[C@@H:46]([O:47][C:48]([CH3:50])=[O:49])[C@:45]([OH:55])([C:51]([O:53][CH3:54])=[O:52])[C@H:44]3[C@@:34]4([C:37]5[CH:38]=[CH:39][C:40]([O:57][CH3:58])=[CH:41][C:42]=5[N:43]3[CH3:56])[CH2:35][CH2:36][N:32]([C@@H:33]14)[CH2:31][CH:30]=[CH:29]2>>[CH3:1][CH2:2][C:3]1[CH2:8][N:9]2[CH2:10][C@@H:5]([CH2:6][C@:7]([C:22]([O:24][CH3:25])=[O:23])([C:39]3[CH:38]=[C:37]4[C@@:34]56[C@@H:44]([N:43]([CH3:56])[C:42]4=[CH:41][C:40]=3[O:57][CH3:58])[C@@:45]([OH:55])([C:51]([O:53][CH3:54])=[O:52])[C@H:46]([O:47][C:48]([CH3:50])=[O:49])[C@:28]3([CH2:27][CH3:26])[CH:29]=[CH:30][CH2:31][N:32]([C@H:33]53)[CH2:36][CH2:35]6)[C:14]3[NH:15][C:16]4[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:13]=3[CH2:12][CH2:11]2)[CH:4]=1

Komponenten

3

Edukt 2

HCID 16596Aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methyl-, methyl ester, (2beta,3beta,4beta,5alpha,12beta,19alpha)-HCID 5458190(+)-Catharanthine

Produkt 1

HCID 4433243',4'-Anhydrovinblastine

Versuchsvorschrift

In J. Am. Chem. Soc./98:22/Oct. 27, 1976, Langlois et al describe a process in which the monomers catharanthine and vindoline are coupled to form AVLB. The coupling is performed using a peracid to generate first the N-oxide of catharanthine, followed by Polonovski-type fragmentation of the N-oxide initiated with addition of trifluoroacetic anhydride to form a dimer. A reducing agent such as sodium borohydride is then added to generate AVLB which can be isolated e.g. chromatographically.

Quellen und Nachweise

ORD-Eintrag
ord-e7abaf1b05c040e8a2584989826f2ee9
Quelldatensatz
uspto-grants-1991_07
Patentnummer
US05034320

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