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A cascade approach to the synthesis of 5-(indol-3-yl)hydantoin framework has been developed by the reaction of indole with glyoxylic acid/pyruvic acid under a deep eutectic solution, (+)-tartaric acid-dimethylurea. N,N'-Dimethylurea from a deep eutectic solution functions as a reactant as well as a solvent mixture. Isolation of the intermediate, 5-hydroxyhydantoin, and its reaction with indole provides the mechanistic evidence for this reaction. This method was successfully applied in the first total synthesis of an alkaloid, (±)-oxoaplysinopsin B, with an overall yield of 48%.

Citation

Ponnusamy Pon Sathieshkumar, Metlapalli Durga Anand Saibabu, Rajagopal Nagarajan. A Cascade Approach for the Synthesis of 5-(Indol-3-yl)hydantoin: An Application to the Total Synthesis of (±)-Oxoaplysinopsin B. The Journal of organic chemistry. 2021 Mar 05;86(5):3730-3740

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PMID: 33599509

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