Structure-Elucidating Total Synthesis of the (Polyenoyl)tetramic Acid Militarinone C§
The (polyenoyl)tetramic acid militarinone C (1) heads a family of seven members. Before our work, the configuration of C-5 was unknown whereas the configurations of C-8' and C-10' were either (R,R) or (S,S). We synthesized the four stereoisomers of constitution 1, which conform with these insights. This included cross-coupling both enantiomers of the western building block (8) with both enantiomers of the eastern building block (9). The specific rotations of the resulting 1 isomers suggested that natural 1 is configured like the coupling partners (S)-8 and (R,R)-9. This conclusion was corroborated by degrading natural 1 to alcohol 35 and by proving its configurational identity with synthetic (R,R)-35.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2020 |
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| Erschienen: |
2020 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:22 |
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| Enthalten in: |
Organic letters - 22(2020), 7 vom: 03. Apr., Seite 2559-2563 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Drescher, Christian [VerfasserIn] |
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| Links: |
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| Themen: |
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| Anmerkungen: |
Date Completed 21.09.2020 Date Revised 21.09.2020 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1021/acs.orglett.0c00431 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM30777919X |
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| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a The (polyenoyl)tetramic acid militarinone C (1) heads a family of seven members. Before our work, the configuration of C-5 was unknown whereas the configurations of C-8' and C-10' were either (R,R) or (S,S). We synthesized the four stereoisomers of constitution 1, which conform with these insights. This included cross-coupling both enantiomers of the western building block (8) with both enantiomers of the eastern building block (9). The specific rotations of the resulting 1 isomers suggested that natural 1 is configured like the coupling partners (S)-8 and (R,R)-9. This conclusion was corroborated by degrading natural 1 to alcohol 35 and by proving its configurational identity with synthetic (R,R)-35 | ||
| 650 | 4 | |a Journal Article | |
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| 700 | 1 | |a Potterat, Olivier |e verfasserin |4 aut | |
| 700 | 1 | |a Hamburger, Matthias |e verfasserin |4 aut | |
| 700 | 1 | |a Brückner, Reinhard |e verfasserin |4 aut | |
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