Total synthesis of euplectin, a natural product with a chromone fused indenone
The first total synthesis of euplectin, a rare metabolite with a chromone annulated indenone motif, has been accomplished in 17 steps. This has been possible through interplay among three key reactions: a Hauser sulfoxide annulation, a new chromone formation and a late-stage retro-Diels-Alder reaction. The entire regiochemical integrity of the successful route is established by an iodine-catalyzed aromatization of a cyclohexane-1,3-dione and the Hauser annulation.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2009 |
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| Erschienen: |
2009 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:11 |
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| Enthalten in: |
Organic letters - 11(2009), 19 vom: 01. Okt., Seite 4398-401 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Mal, Dipakranjan [VerfasserIn] |
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| Links: |
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| Themen: |
Biological Factors |
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| Anmerkungen: |
Date Completed 01.12.2009 Date Revised 24.09.2009 published: Print Citation Status MEDLINE |
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| doi: |
10.1021/ol901817r |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM191199966 |
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| 520 | |a The first total synthesis of euplectin, a rare metabolite with a chromone annulated indenone motif, has been accomplished in 17 steps. This has been possible through interplay among three key reactions: a Hauser sulfoxide annulation, a new chromone formation and a late-stage retro-Diels-Alder reaction. The entire regiochemical integrity of the successful route is established by an iodine-catalyzed aromatization of a cyclohexane-1,3-dione and the Hauser annulation | ||
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