Stereostructure Clarifying Total Synthesis of the (Polyenoyl)tetramic Acid Militarinone B. A Highly Acid-Labile N-Protecting Group for Amides†
The 5S, 8'R, and 10'R configurations of militarinone B (3), which is a natural product from Paecilomyces militaris, should equal those in its biosynthetic precursor, militarinone C. The configuration at C-1' emerged from syntheses of the militarinone B candidates 1''S- and 1''R-(5S,8'R,10'R)-3 from the building blocks 9, 11, 14, and 15a while introducing TMB as a more acid-labile N-protecting group for β-ketoamides than DMB. Comparisons of 1''S- and 1''R-(5S,8'R,10'R)-3 with natural militarinone B (3; reisolated from Nature) revealed identity versus distinctness.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2021 |
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| Erschienen: |
2021 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:23 |
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| Enthalten in: |
Organic letters - 23(2021), 16 vom: 20. Aug., Seite 6194-6199 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Drescher, Christian [VerfasserIn] |
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| Links: |
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| Themen: |
503-83-3 |
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| Anmerkungen: |
Date Completed 19.11.2021 Date Revised 19.11.2021 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1021/acs.orglett.1c01652 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM328689599 |
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| 520 | |a The 5S, 8'R, and 10'R configurations of militarinone B (3), which is a natural product from Paecilomyces militaris, should equal those in its biosynthetic precursor, militarinone C. The configuration at C-1' emerged from syntheses of the militarinone B candidates 1''S- and 1''R-(5S,8'R,10'R)-3 from the building blocks 9, 11, 14, and 15a while introducing TMB as a more acid-labile N-protecting group for β-ketoamides than DMB. Comparisons of 1''S- and 1''R-(5S,8'R,10'R)-3 with natural militarinone B (3; reisolated from Nature) revealed identity versus distinctness | ||
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