Application of a Raney-Cobalt-Mediated Tandem Reductive Cyclization Protocol to Total Syntheses of the Aspidosperma Alkaloids (±)-Limaspermidine and (±)-1-Acetylaspidoalbidine

Application of a Raney-Cobalt-Mediated Tandem Reductive Cyclization Protocol to Total Syntheses of the Aspidosperma Alkaloids (±)-Limaspermidine and (±)-1-Acetylaspidoalbidine

The racemic modification of the Aspidosperma alkaloid limaspermidine (1) has been prepared in ten steps including one involving a Raney-cobalt-mediated tandem reductive cyclization of nitrile 8 to give the tetracyclic system 9b. Compound (±)-1 has been converted over two steps into (±)-1-acetylaspid...

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Veröffentlicht in:Organic letters 2012-11, Vol.14 (22), p.5621-5623
Hauptverfasser: Tan, Shen H, Banwell, Martin G, Willis, Anthony C, Reekie, Tristan A
Format: Artikel
Sprache:eng
Schlagworte:
Aspidosperma - chemistry
Carbazoles
Chemistry, Organic - methods
Cobalt - chemistry
Cyclization
Indole Alkaloids - chemical synthesis
Indole Alkaloids - chemistry
Molecular Structure
Nitriles - chemistry
Plant Bark - chemistry
Stereoisomerism
Venezuela
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Zusammenfassung:The racemic modification of the Aspidosperma alkaloid limaspermidine (1) has been prepared in ten steps including one involving a Raney-cobalt-mediated tandem reductive cyclization of nitrile 8 to give the tetracyclic system 9b. Compound (±)-1 has been converted over two steps into (±)-1-acetylaspidoalbidine [(±)-13].
ISSN:1523-7060
1523-7052
DOI:10.1021/ol3026846