Total synthesis of basiliskamides A and B
[structure: see text] The first enantioselective synthesis of the polyketide antibiotics basiliskamides A and B, which exhibit potent in vivo activity against Candida albicans and Aspergillus fumigatus, has been achieved. Serial asymmetric crotylsilane and crotylboronate additions established the C7-C10 stereochemical tetrad. Takai iodoolefination and palladium-mediated cross-coupling were used to install the (Z,E)-vinyl acrylamide. Spectroscopic data is consistent with the assignment of the absolute configurations of the natural products as (7S,8S,9R,10S).
| Medienart: |
Artikel |
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| Erscheinungsjahr: |
2004 |
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| Erschienen: |
2004 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:6 |
|---|---|
| Enthalten in: |
Organic letters - 6(2004), 20 vom: 30. Sept., Seite 3533-6 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Lipomi, Darren J [VerfasserIn] |
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| Anmerkungen: |
Date Completed 31.10.2005 Date Revised 15.11.2012 published: Print Citation Status MEDLINE |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM150615825 |
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| 100 | 1 | |a Lipomi, Darren J |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Total synthesis of basiliskamides A and B |
| 264 | 1 | |c 2004 | |
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a ohne Hilfsmittel zu benutzen |b n |2 rdamedia | ||
| 338 | |a Band |b nc |2 rdacarrier | ||
| 500 | |a Date Completed 31.10.2005 | ||
| 500 | |a Date Revised 15.11.2012 | ||
| 500 | |a published: Print | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a [structure: see text] The first enantioselective synthesis of the polyketide antibiotics basiliskamides A and B, which exhibit potent in vivo activity against Candida albicans and Aspergillus fumigatus, has been achieved. Serial asymmetric crotylsilane and crotylboronate additions established the C7-C10 stereochemical tetrad. Takai iodoolefination and palladium-mediated cross-coupling were used to install the (Z,E)-vinyl acrylamide. Spectroscopic data is consistent with the assignment of the absolute configurations of the natural products as (7S,8S,9R,10S) | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Research Support, N.I.H., Extramural | |
| 650 | 4 | |a Research Support, Non-U.S. Gov't | |
| 650 | 4 | |a Research Support, U.S. Gov't, P.H.S. | |
| 650 | 7 | |a Amides |2 NLM | |
| 650 | 7 | |a Antifungal Agents |2 NLM | |
| 650 | 7 | |a Biological Factors |2 NLM | |
| 650 | 7 | |a Polyketides |2 NLM | |
| 650 | 7 | |a basiliskamide A |2 NLM | |
| 650 | 7 | |a basiliskamide B |2 NLM | |
| 700 | 1 | |a Langille, Neil F |e verfasserin |4 aut | |
| 700 | 1 | |a Panek, James S |e verfasserin |4 aut | |
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