Towards the core structure of Strychnos alkaloids using samarium diiodide-induced reactions of indole derivatives.
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Publication Details
Output type: Journal article
Author list: Beemelmanns, Gross, Reissig
Publisher: Wiley
Publication year: 2013
Journal: Chemistry - A European Journal (0947-6539)
Volume number: 19
Issue number: 52
Start page: 17801
End page: 8
Number of pages: -17792
ISSN: 0947-6539
eISSN: 1521-3765
Languages: English-Great Britain (EN-GB)
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Open access status: closed
Abstract
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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