Total synthesis of (+)-ambruticin S : probing the pharmacophoric subunit
An enantioselective synthesis of the antifungal natural product (+)-ambruticin S has been accomplished starting with the readily available methyl alpha-d-glucopyranoside, (R)-Roche ester, and (S)-glycidol as chirons, which encompassed seven of the 10 stereogenic centers of the target molecule. The remaining three centers were set by a highly diastereoselective, asymmetric cyclopropanation employing a chiral, nonracemic phosphonamide reagent. Our strategy for the construction of the dihydropyran subunit involved a highly syn-selective Lewis acid catalyzed 6-endo-trig cyclization. Other key steps in the synthesis featured an epoxide opening with a dithiane anion, two efficient phosphonamide-anion based olefinations, and a late-stage C-glycosylation.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2010 |
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| Erschienen: |
2010 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:75 |
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| Enthalten in: |
The Journal of organic chemistry - 75(2010), 16 vom: 20. Aug., Seite 5601-18 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Hanessian, Stephen [VerfasserIn] |
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| Links: |
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| Themen: |
Ambruticin |
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| Anmerkungen: |
Date Completed 24.11.2010 Date Revised 19.11.2015 published: Print Citation Status MEDLINE |
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| doi: |
10.1021/jo100956v |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM20026530X |
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| 245 | 1 | 0 | |a Total synthesis of (+)-ambruticin S |b probing the pharmacophoric subunit |
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| 500 | |a Date Completed 24.11.2010 | ||
| 500 | |a Date Revised 19.11.2015 | ||
| 500 | |a published: Print | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a An enantioselective synthesis of the antifungal natural product (+)-ambruticin S has been accomplished starting with the readily available methyl alpha-d-glucopyranoside, (R)-Roche ester, and (S)-glycidol as chirons, which encompassed seven of the 10 stereogenic centers of the target molecule. The remaining three centers were set by a highly diastereoselective, asymmetric cyclopropanation employing a chiral, nonracemic phosphonamide reagent. Our strategy for the construction of the dihydropyran subunit involved a highly syn-selective Lewis acid catalyzed 6-endo-trig cyclization. Other key steps in the synthesis featured an epoxide opening with a dithiane anion, two efficient phosphonamide-anion based olefinations, and a late-stage C-glycosylation | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Research Support, Non-U.S. Gov't | |
| 650 | 7 | |a Antifungal Agents |2 NLM | |
| 650 | 7 | |a Biological Factors |2 NLM | |
| 650 | 7 | |a Pyrans |2 NLM | |
| 650 | 7 | |a ambruticin S |2 NLM | |
| 650 | 7 | |a ambruticin |2 NLM | |
| 650 | 7 | |a X794618736 |2 NLM | |
| 700 | 1 | |a Focken, Thilo |e verfasserin |4 aut | |
| 700 | 1 | |a Mi, Xueling |e verfasserin |4 aut | |
| 700 | 1 | |a Oza, Rupal |e verfasserin |4 aut | |
| 700 | 1 | |a Chen, Bin |e verfasserin |4 aut | |
| 700 | 1 | |a Ritson, Dougal |e verfasserin |4 aut | |
| 700 | 1 | |a Beaudegnies, Renaud |e verfasserin |4 aut | |
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