1402730-53-3Relevant academic research and scientific papers
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.
, p. 9601 - 9611 (2012/09/07)
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. [Metal]-mediated: Methods for the addition of indoles to isatogens have been developed to prepare 2,2-disubstituted indolin-3-ones. The total synthesis of 13-deoxy-isatisine has been executed (see scheme) by featuring several [metal]-mediated reactions at the final stages, such as Sonogashira coupling, [Pd]-mediated nitro-alkyne cycloisomerization, and [In]-mediated addition of indole to an isatogen. Copyright
