Synthesis of vinca alkaloids and related compounds. 100. Stereoselective oxidation reactions of compounds with the aspidospermane and quebrachamine ring system. First synthesis of some alkaloids containing the epoxy ring

The first syntheses of the alkaloids (-)-mehranine (3), (+)-voaphylline/conoflorine (4), (+)-N(a)-methylvoaphylline/hecubine (5), and (-)-lochnericine (2) were achieved by stereoselective epoxidation starting from (-)-tabersonine (1), through intermediates with the aspidospermane and quebrachamine s...

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Veröffentlicht in:	Journal of organic chemistry 2002-10, Vol.67 (21), p.7255-7260
Hauptverfasser:	ELES, Janos, KALAUS, György, GREINER, Istvan, KAJTAR-PEREDY, Maria, SZABO, Pal, MIKLOS KESERU, György, SZABO, Lajos, SZANTAY, Csaba
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkaloids - chemical synthesis Alkaloids - chemistry Chemistry Epoxy Compounds - chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Indicators and Reagents Indole Alkaloids Indoles - chemistry Models, Molecular Molecular Conformation Organic chemistry Oxidation-Reduction Preparations and properties Quinolines Stereoisomerism Vinca Alkaloids - chemical synthesis Vinca Alkaloids - chemistry
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Zusammenfassung:	The first syntheses of the alkaloids (-)-mehranine (3), (+)-voaphylline/conoflorine (4), (+)-N(a)-methylvoaphylline/hecubine (5), and (-)-lochnericine (2) were achieved by stereoselective epoxidation starting from (-)-tabersonine (1), through intermediates with the aspidospermane and quebrachamine skeleton.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo020386r