Total Synthesis of (±)-Impatien A via Aza-Heck Cyclization
The first total synthesis of the natural product impatien A is described. This concise synthesis features an aza-Heck cyclization to construct the complex spirocyclic ring system and provides a rare example of the use of aza-Heck cyclizations in complex molecule synthesis. To enable this key cyclization of an electrophilic nitrogen atom with a tetrasubstituted alkene, we utilized high-throughput experimentation to identify a new ligand and ultimately deliver impatien A in seven steps from known compounds.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2021 |
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| Erschienen: |
2021 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:23 |
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| Enthalten in: |
Organic letters - 23(2021), 18 vom: 17. Sept., Seite 7285-7289 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Korch, Katerina M [VerfasserIn] |
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| Links: |
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| Themen: |
Biological Products |
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| Anmerkungen: |
Date Completed 18.01.2022 Date Revised 18.09.2022 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1021/acs.orglett.1c02767 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM330030426 |
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| 500 | |a Date Revised 18.09.2022 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a The first total synthesis of the natural product impatien A is described. This concise synthesis features an aza-Heck cyclization to construct the complex spirocyclic ring system and provides a rare example of the use of aza-Heck cyclizations in complex molecule synthesis. To enable this key cyclization of an electrophilic nitrogen atom with a tetrasubstituted alkene, we utilized high-throughput experimentation to identify a new ligand and ultimately deliver impatien A in seven steps from known compounds | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Research Support, N.I.H., Extramural | |
| 650 | 4 | |a Research Support, Non-U.S. Gov't | |
| 650 | 4 | |a Research Support, U.S. Gov't, Non-P.H.S. | |
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