Enantioselective synthesis of (+)-obolactone based on a symmetry-breaking Wacker monooxidation of a diene
A concise synthesis of the dihydro-α-pyrone/dihydro-γ-pyrone natural product (+)-obolactone (13) is disclosed. The dienediol acetonide 23 (≥97% ee) was obtained from 1,5-dichloropentane-2,4-dione in four steps. A Wacker monooxidation of 23 furnished the monoketone 24 in 64% yield. The OH group of the ensuing dihydro-γ-pyrone 31 was esterified under Mitsunobu conditions with cinnamic acid (→ 80% inversion and 20% retention of configuration). A ring-closing metathesis formed the dihydro-α-pyrone moiety of the target in the terminating step.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2013 |
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| Erschienen: |
2013 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:15 |
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| Enthalten in: |
Organic letters - 15(2013), 6 vom: 15. März, Seite 1294-7 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Walleser, Patrick [VerfasserIn] |
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| Links: |
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| Themen: |
Biological Products |
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| Anmerkungen: |
Date Completed 24.07.2013 Date Revised 21.11.2013 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1021/ol400232m |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM225428393 |
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| 245 | 1 | 0 | |a Enantioselective synthesis of (+)-obolactone based on a symmetry-breaking Wacker monooxidation of a diene |
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| 500 | |a Date Revised 21.11.2013 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a A concise synthesis of the dihydro-α-pyrone/dihydro-γ-pyrone natural product (+)-obolactone (13) is disclosed. The dienediol acetonide 23 (≥97% ee) was obtained from 1,5-dichloropentane-2,4-dione in four steps. A Wacker monooxidation of 23 furnished the monoketone 24 in 64% yield. The OH group of the ensuing dihydro-γ-pyrone 31 was esterified under Mitsunobu conditions with cinnamic acid (→ 80% inversion and 20% retention of configuration). A ring-closing metathesis formed the dihydro-α-pyrone moiety of the target in the terminating step | ||
| 650 | 4 | |a Journal Article | |
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| 650 | 7 | |a Polyenes |2 NLM | |
| 650 | 7 | |a obolactone |2 NLM | |
| 700 | 1 | |a Brückner, Reinhard |e verfasserin |4 aut | |
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