Reductive Radical Annulation Strategy toward Bicyclo[3.2.1]octanes : Synthesis of ent-Kaurane and Beyerane Diterpenoids
Here we report a general [3 + 2] radical annulation that allows the facile construction of bicyclo[3.2.1]octane motifs in ent-kaurane- and beyerane-type diterpenoids. This radical annulation is difficult to control but was realized by harnessing an unprecedented and counterintuitive effect of TEMPO. Eleven natural products with a wide array of oxidation states are easily prepared, demonstrating the powerful utility of this straightforward synthetic strategy.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2022 |
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| Erschienen: |
2022 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:144 |
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| Enthalten in: |
Journal of the American Chemical Society - 144(2022), 1 vom: 12. Jan., Seite 99-105 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Zhuo, Junming [VerfasserIn] |
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| Anmerkungen: |
Date Completed 04.02.2022 Date Revised 04.02.2022 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1021/jacs.1c11623 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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NLM334944252 |
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| 520 | |a Here we report a general [3 + 2] radical annulation that allows the facile construction of bicyclo[3.2.1]octane motifs in ent-kaurane- and beyerane-type diterpenoids. This radical annulation is difficult to control but was realized by harnessing an unprecedented and counterintuitive effect of TEMPO. Eleven natural products with a wide array of oxidation states are easily prepared, demonstrating the powerful utility of this straightforward synthetic strategy | ||
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| 700 | 1 | |a Wu, Jinbao |e verfasserin |4 aut | |
| 700 | 1 | |a Li, Zijian |e verfasserin |4 aut | |
| 700 | 1 | |a Li, Chao |e verfasserin |4 aut | |
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