Scalable Total Synthesis of Acremolactone B
© 2023 Wiley-VCH GmbH..
Acremolactone B is a pyridine-containing azaphilone-type polyketide with herbicidal activity. We developed an aza-6π electrocyclization-aromatization strategy to construct the tetrasubstituted pyridine ring and achieved the first total synthesis of this molecule on a gram scale. A bicyclic intermediate was expeditiously prepared by using [2 + 2] photocycloaddition and chemoselective Baeyer-Villiger oxidation, which was further elaborated to a densely substituted aza-triene. An electrocyclization-aromatization cascade was exploited to forge the tetracyclic core of the natural product, and the side chain was introduced through diastereoselective acylation and reduction.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2023 |
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| Erschienen: |
2023 |
| Enthalten in: |
Zur Gesamtaufnahme - year:2023 |
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| Enthalten in: |
Angewandte Chemie (International ed. in English) - (2023) vom: 06. Nov., Seite e202314800 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Ba, Mengyu [VerfasserIn] |
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| Links: |
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| Themen: |
Aza-6π electrocyclization |
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| Anmerkungen: |
Date Revised 07.11.2023 published: Print-Electronic Citation Status Publisher |
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| doi: |
10.1002/anie.202314800 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM364247096 |
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| 520 | |a Acremolactone B is a pyridine-containing azaphilone-type polyketide with herbicidal activity. We developed an aza-6π electrocyclization-aromatization strategy to construct the tetrasubstituted pyridine ring and achieved the first total synthesis of this molecule on a gram scale. A bicyclic intermediate was expeditiously prepared by using [2 + 2] photocycloaddition and chemoselective Baeyer-Villiger oxidation, which was further elaborated to a densely substituted aza-triene. An electrocyclization-aromatization cascade was exploited to forge the tetracyclic core of the natural product, and the side chain was introduced through diastereoselective acylation and reduction | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a aza-6π electrocyclization | |
| 650 | 4 | |a azaphilones | |
| 650 | 4 | |a gram-scale synthesis | |
| 650 | 4 | |a herbicides | |
| 650 | 4 | |a multisubstituted pyridines | |
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| 700 | 1 | |a Ren, Lu |e verfasserin |4 aut | |
| 700 | 1 | |a Whittingham, William |e verfasserin |4 aut | |
| 700 | 1 | |a Yang, Peng |e verfasserin |4 aut | |
| 700 | 1 | |a Li, Ang |e verfasserin |4 aut | |
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