A serendipitous synthesis of (+)-gregatin B, second structure revisions of the aspertetronins, gregatins, and graminin A, structure revision of the penicilliols
A (DHQN)(2)AQN-promoted asymmetric dihydroxylation (92% ee) of the allyl chloride derived from enynol (E)-13 and an 8-step sequence provided access to the hydroxyethylated furanone (R)-21. Oxidation with MnO(2) furnished 50% furanone (+)-(R)-2a and 2.7% isomeric furanone (+)-(R)-3a. (R)-2a possesses the accepted constitution of (+)-gregatin B but its spectra are different. Surprisingly, (+)-(R)-3a equals the natural product. Analogous structure reassignments are due for the gregatins A and C-E, the aspertetronins A-B, graminin A, and the penicilliols A and B.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2011 |
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| Erschienen: |
2011 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:13 |
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| Enthalten in: |
Organic letters - 13(2011), 10 vom: 20. Mai, Seite 2730-3 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Burghart-Stoll, Heike [VerfasserIn] |
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| Links: |
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| Themen: |
676XIY14LM |
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| Anmerkungen: |
Date Completed 26.07.2011 Date Revised 11.01.2019 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1021/ol2008318 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM207795525 |
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| 100 | 1 | |a Burghart-Stoll, Heike |e verfasserin |4 aut | |
| 245 | 1 | 2 | |a A serendipitous synthesis of (+)-gregatin B, second structure revisions of the aspertetronins, gregatins, and graminin A, structure revision of the penicilliols |
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| 500 | |a Date Completed 26.07.2011 | ||
| 500 | |a Date Revised 11.01.2019 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a A (DHQN)(2)AQN-promoted asymmetric dihydroxylation (92% ee) of the allyl chloride derived from enynol (E)-13 and an 8-step sequence provided access to the hydroxyethylated furanone (R)-21. Oxidation with MnO(2) furnished 50% furanone (+)-(R)-2a and 2.7% isomeric furanone (+)-(R)-3a. (R)-2a possesses the accepted constitution of (+)-gregatin B but its spectra are different. Surprisingly, (+)-(R)-3a equals the natural product. Analogous structure reassignments are due for the gregatins A and C-E, the aspertetronins A-B, graminin A, and the penicilliols A and B | ||
| 650 | 4 | |a Journal Article | |
| 650 | 7 | |a Allyl Compounds |2 NLM | |
| 650 | 7 | |a Furans |2 NLM | |
| 650 | 7 | |a Lactones |2 NLM | |
| 650 | 7 | |a gregatin B |2 NLM | |
| 650 | 7 | |a penicilliol A |2 NLM | |
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| 650 | 7 | |a allyl chloride |2 NLM | |
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