TCCA-mediated oxidative rearrangement of tetrahydro-β-carbolines : facile access to spirooxindoles and the total synthesis of (±)-coerulescine and (±)-horsfiline
This journal is © The Royal Society of Chemistry..
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.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2021 |
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| Erschienen: |
2021 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:11 |
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| Enthalten in: |
RSC advances - 11(2021), 27 vom: 30. Apr., Seite 16537-16546 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Sathish, Manda [VerfasserIn] |
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| Links: |
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| Anmerkungen: |
Date Revised 16.07.2022 published: Electronic-eCollection Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1039/d1ra02381k |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| 500 | |a published: Electronic-eCollection | ||
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| 520 | |a This journal is © The Royal Society of Chemistry. | ||
| 520 | |a 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 | ||
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| 700 | 1 | |a Nachtigall, Fabiane M |e verfasserin |4 aut | |
| 700 | 1 | |a Santos, Leonardo S |e verfasserin |4 aut | |
| 700 | 1 | |a Shankaraiah, Nagula |e verfasserin |4 aut | |
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