Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 19, Issue 52, Pages 17801-17808Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201302795
Keywords
alkaloids; Barbier reaction; cascade reaction; indole; samarium diiodide
Categories
Funding
- Volkswagen Stiftung
- Deutsche Forschungsgemeinschaft
- Fonds der Chemischen Industrie
- Studienstiftung des Deutschen Volkes
- Ernst Schering Research Foundation
- Bayer HealthCare
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This report describes the development of a first and second generation approach towards the synthesis of the ABCEG pentacyclic core structure of Strychnos alkaloids. First, we discuss a sequential approach applying a series of functional group transformations to prepare suitable precursors for cyclization reactions. These include attempts of samarium diiodide-induced cyclizations or a Barbier-type reaction of a transient lithium organyl, which successfully led to a tetracyclic key building block earlier used for the synthesis of strychnine. Secondly, we account our first steps towards the development of an atom-economical samarium diiodide-induced cascade reaction using dimeric indolyl ketones as cyclization precursors. In this context, we discuss plausible mechanisms for the samarium diiodide-induced cascade reaction as well as transformations of the obtained tetracyclic dihydroindoline derivatives.
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