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TCCA-mediated oxidative rearrangement of tetrahydro-β-carbolines: Facile access to spirooxindoles and the total synthesis of (±)-coerulescine and (±)-horsfiline
dc.contributor.author | Sathish, Manda | |
dc.contributor.author | Sakla, Akash P. | |
dc.contributor.author | Nachtigall, Fabiane Manke | |
dc.contributor.author | Santos, Leonardo S. | |
dc.contributor.author | Shankaraiah, N. | |
dc.date.accessioned | 2021-05-24T23:22:17Z | |
dc.date.available | 2021-05-24T23:22:17Z | |
dc.date.issued | 2021-04-15 | |
dc.identifier | 10.1039/d1ra02381k | |
dc.identifier.issn | 20462069 | |
dc.identifier.uri | https://hdl.handle.net/20.500.12728/8883 | |
dc.description.abstract | Multi-reactive centered reagents are beneficial in chemical synthesis due to their advantage of minimal material utilization and formation of less by-products. Trichloroisocyanuric acid (TCCA), a reagent with three reactive centers, was employed in the synthesis of spirooxindoles through the oxidative rearrangement of various N-protected tetrahydro-β-carbolines. In this protocol, low equivalents of TCCA were required to access spirooxindoles (up to 99% yield) with a wide substrate scope. Furthermore, the applicability and robustness of this protocol were proven for the gram-scale total synthesis of natural alkaloids such as (±)-coerulescine (1) and (±)-horsfiline (2) in excellent yields. | es_ES |
dc.language.iso | en | es_ES |
dc.publisher | Royal Society of Chemistry | es_ES |
dc.subject | Pyridine | es_ES |
dc.subject | Reagents | es_ES |
dc.title | TCCA-mediated oxidative rearrangement of tetrahydro-β-carbolines: Facile access to spirooxindoles and the total synthesis of (±)-coerulescine and (±)-horsfiline | es_ES |
dc.type | Article | es_ES |