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 Ring1a

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 sk...

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Published in:Journal of organic chemistry 2002-10, Vol.67 (21), p.7255-7260
Main Authors: Éles, János, Kalaus, György, Greiner, István, Kajtár-Peredy, Mária, Szabó, Pál, Keserû, György Miklós, Szabó, Lajos, Szántay, Csaba
Format: Article
Language:English
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Summary: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