Short, Enantioselective Total Synthesis of Stephacidin A

Short, Enantioselective Total Synthesis of Stephacidin A

A concise route to the heptacyclic indole alkaloid stephacidin A (1) includes a simple method for the gram‐scale synthesis of substituted tryptophans, a remarkable indole annulation, and the first enolate coupling of an amide to an ester. This synthesis secures the relative configuration of the natu...

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Veröffentlicht in:Angewandte Chemie International Edition 2005-01, Vol.44 (4), p.606-609
Hauptverfasser: Baran, Phil S., Guerrero, Carlos A., Ambhaikar, Narendra B., Hafensteiner, Benjamin D.
Format: Artikel
Sprache:eng
Schlagworte:
alkaloids
cascade reactions
Indole Alkaloids
indoles
Indoles - chemical synthesis
Molecular Structure
natural products
Stereoisomerism
total synthesis
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Beschreibung
Zusammenfassung:A concise route to the heptacyclic indole alkaloid stephacidin A (1) includes a simple method for the gram‐scale synthesis of substituted tryptophans, a remarkable indole annulation, and the first enolate coupling of an amide to an ester. This synthesis secures the relative configuration of the natural product and paves a potential path to several of its congeners.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200461864