InCl3-Mediated Addition of Indole to Isatogens: An Expeditious Synthesis of 13-deoxy-Isatisine A

Kumar, Chepuri V. Suneel ; Puranik, Vedavati G ; Ramana, Chepuri V. (2012) InCl3-Mediated Addition of Indole to Isatogens: An Expeditious Synthesis of 13-deoxy-Isatisine A Chemistry - A European Journal, 18 (31). pp. 9601-9611. ISSN 0947-6539

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Official URL: http://onlinelibrary.wiley.com/doi/10.1002/chem.20...

Related URL: http://dx.doi.org/10.1002/chem.201103604

Abstract

A strategy directed towards the total synthesis of isatisine A that involves several late-stage metal-catalyzed transformations that address the key carbon–carbon and carbon–heteroatom bond formations has been developed. As a part of this strategy, methods for the addition of indoles to isatogens that lead selectively to either 2,2-disubstituted N-hydroxyindolin-3-one or 2,2-disubstituted indolin-3-one compounds have been developed by employing InCl3 as a catalyst or as the reagent. The present methods provide the first examples of the additions of indoles to the isatogen nucleus. To demonstrate its viability, the synthesis of 13-deoxy-isatisine A has been completed in ten steps from a known and easily available lactone.

Item Type:Article
Source:Copyright of this article belongs to John Wiley & Sons, Inc.
Keywords:Indium; Indoles; Isatogens; Natural Products; Total Synthesis
ID Code:106005
Deposited On:01 Feb 2018 16:53
Last Modified:01 Feb 2018 16:53

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