Enantioselective Total Synthesis of (-)-Hamigeran F and Its Rearrangement Product
Herein, we report the first enantioselective total synthesis of the highly complex hamigeran diterpenoid (-)-hamigeran F and its rearrangement product. The synthetic strategy features key steps of asymmetric hydrogenation, Horner-Wadsworth-Emmons olefination, and intramolecular Friedel-Crafts acylation to construct the [6,6,5]-tricyclic skeleton bearing three consecutive stereocenters, a sequence of steps involving Rosenmund reduction, Wittig reaction, dihydroxylation to assemble the α-acetoxy ketone group, and an intramolecular aldol reaction to build the tetracyclic core structure.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2022 |
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| Erschienen: |
2022 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:24 |
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| Enthalten in: |
Organic letters - 24(2022), 28 vom: 22. Juli, Seite 5161-5165 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Xiong, Ying [VerfasserIn] |
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| Links: |
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| Themen: |
Diterpenes |
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| Anmerkungen: |
Date Completed 25.07.2022 Date Revised 05.08.2022 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1021/acs.orglett.2c01997 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM343364972 |
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| 520 | |a Herein, we report the first enantioselective total synthesis of the highly complex hamigeran diterpenoid (-)-hamigeran F and its rearrangement product. The synthetic strategy features key steps of asymmetric hydrogenation, Horner-Wadsworth-Emmons olefination, and intramolecular Friedel-Crafts acylation to construct the [6,6,5]-tricyclic skeleton bearing three consecutive stereocenters, a sequence of steps involving Rosenmund reduction, Wittig reaction, dihydroxylation to assemble the α-acetoxy ketone group, and an intramolecular aldol reaction to build the tetracyclic core structure | ||
| 650 | 4 | |a Journal Article | |
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| 700 | 1 | |a Li, Tao |e verfasserin |4 aut | |
| 700 | 1 | |a Xie, Jian-Hua |e verfasserin |4 aut | |
| 700 | 1 | |a Zhou, Qi-Lin |e verfasserin |4 aut | |
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