Total synthesis of (-)-brazilane via a lipase-catalyzed desymmetrisation reaction
Herein, we described the asymmetric total synthesis of (-)-brazilane, an optically active natural product. The key steps of this synthetic approach are a lipase-catalyzed desymmetrisation reaction of a prochiral diol using vinyl acetate to prepare a chiral primary alcohol and a trifluoroacetic acid-catalyzed one pot intramolecular tandem Prins/Friedel-Crafts reaction used to construct the cis-fused chromane and indane framework.[Formula: see text].
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2022 |
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| Erschienen: |
2022 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:36 |
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| Enthalten in: |
Natural product research - 36(2022), 20 vom: 15. Okt., Seite 5125-5133 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Guo, Xiaofeng [VerfasserIn] |
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| Links: |
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| Anmerkungen: |
Date Completed 17.10.2022 Date Revised 17.10.2022 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1080/14786419.2021.1922403 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM325223378 |
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| 520 | |a Herein, we described the asymmetric total synthesis of (-)-brazilane, an optically active natural product. The key steps of this synthetic approach are a lipase-catalyzed desymmetrisation reaction of a prochiral diol using vinyl acetate to prepare a chiral primary alcohol and a trifluoroacetic acid-catalyzed one pot intramolecular tandem Prins/Friedel-Crafts reaction used to construct the cis-fused chromane and indane framework.[Formula: see text] | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a (–)-brazilane | |
| 650 | 4 | |a Total synthesis | |
| 650 | 4 | |a lipase-catalyzed desymmetrisation | |
| 650 | 4 | |a natural product | |
| 650 | 4 | |a tandem Prins/Friedel-Crafts reaction | |
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| 650 | 7 | |a Lipase |2 NLM | |
| 650 | 7 | |a EC 3.1.1.3 |2 NLM | |
| 700 | 1 | |a Xue, Zhiwei |e verfasserin |4 aut | |
| 700 | 1 | |a Xu, Dongdong |e verfasserin |4 aut | |
| 700 | 1 | |a Tu, Qidong |e verfasserin |4 aut | |
| 700 | 1 | |a Chang, Honghong |e verfasserin |4 aut | |
| 700 | 1 | |a Yang, Xihua |e verfasserin |4 aut | |
| 700 | 1 | |a Huang, Shuangping |e verfasserin |4 aut | |
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