A Cascade Approach for the Synthesis of 5-(Indol-3-yl)hydantoin: An Application to the Total Synthesis of (±)-Oxoaplysinopsin B
A Cascade Approach for the Synthesis of 5-(Indol-3-yl)hydantoin: An Application to the Total Synthesis of (±)-Oxoaplysinopsin B
| dc.contributor.author | Sathieshkumar, Ponnusamy Pon | |
| dc.contributor.author | Anand Saibabu, Metlapalli Durga | |
| dc.contributor.author | Nagarajan, Rajagopal | |
| dc.date.accessioned | 2022-03-27T08:39:49Z | |
| dc.date.available | 2022-03-27T08:39:49Z | |
| dc.date.issued | 2021-03-05 | |
| dc.description.abstract | 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%. | |
| dc.identifier.citation | Journal of Organic Chemistry. v.86(5) | |
| dc.identifier.issn | 00223263 | |
| dc.identifier.uri | 10.1021/acs.joc.0c02435 | |
| dc.identifier.uri | https://pubs.acs.org/doi/10.1021/acs.joc.0c02435 | |
| dc.identifier.uri | https://dspace.uohyd.ac.in/handle/1/11412 | |
| dc.title | A Cascade Approach for the Synthesis of 5-(Indol-3-yl)hydantoin: An Application to the Total Synthesis of (±)-Oxoaplysinopsin B | |
| dc.type | Journal. Article | |
| dspace.entity.type |
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