Stereoselective syntheses of dihydroxerulin and xerulinic acid, anti-hypocholesterolemic dyes from the fungus Xerula melanotricha
The title compounds 2 and 3, which are inhibitors of the biosynthesis of cholesterol, were synthesized in a convergent and perfectly stereoselective manner. In the key step, bromobutenolide 6 (obtained from levulinic acid in two steps) was coupled with either of the novel bis(stannanes) trans,cis,trans-35 or trans,trans,trans-35 [each accessible from 3-(tributylstannyl)allyl alcohol (17) in four steps], giving gamma-alkylidenebutenolide trans,trans,trans-32. This compound was coupled with iododiyne 42 or the bromoenediynoate 44 leading to dihydroxerulin (2) and to the (trimethylsilylethyl)ester 45 of xerulinic acid, respectively. Deprotection of the latter provided totally synthetic xerulinic acid (3) for the first time.
| Medienart: |
Artikel |
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| Erscheinungsjahr: |
2005 |
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| Erschienen: |
2005 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:11 |
|---|---|
| Enthalten in: |
Chemistry (Weinheim an der Bergstrasse, Germany) - 11(2005), 5 vom: 18. Feb., Seite 1610-24 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Sorg, Achim [VerfasserIn] |
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| Themen: |
132971-60-9 |
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| Anmerkungen: |
Date Completed 20.06.2006 Date Revised 04.08.2009 published: Print Citation Status MEDLINE |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM153286636 |
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| 100 | 1 | |a Sorg, Achim |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Stereoselective syntheses of dihydroxerulin and xerulinic acid, anti-hypocholesterolemic dyes from the fungus Xerula melanotricha |
| 264 | 1 | |c 2005 | |
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a ohne Hilfsmittel zu benutzen |b n |2 rdamedia | ||
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| 500 | |a Date Completed 20.06.2006 | ||
| 500 | |a Date Revised 04.08.2009 | ||
| 500 | |a published: Print | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a The title compounds 2 and 3, which are inhibitors of the biosynthesis of cholesterol, were synthesized in a convergent and perfectly stereoselective manner. In the key step, bromobutenolide 6 (obtained from levulinic acid in two steps) was coupled with either of the novel bis(stannanes) trans,cis,trans-35 or trans,trans,trans-35 [each accessible from 3-(tributylstannyl)allyl alcohol (17) in four steps], giving gamma-alkylidenebutenolide trans,trans,trans-32. This compound was coupled with iododiyne 42 or the bromoenediynoate 44 leading to dihydroxerulin (2) and to the (trimethylsilylethyl)ester 45 of xerulinic acid, respectively. Deprotection of the latter provided totally synthetic xerulinic acid (3) for the first time | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Research Support, Non-U.S. Gov't | |
| 650 | 7 | |a Alkynes |2 NLM | |
| 650 | 7 | |a Diynes |2 NLM | |
| 650 | 7 | |a Lactones |2 NLM | |
| 650 | 7 | |a Tin Compounds |2 NLM | |
| 650 | 7 | |a dihydroxerulin |2 NLM | |
| 650 | 7 | |a 132971-60-9 |2 NLM | |
| 650 | 7 | |a xerulinic acid |2 NLM | |
| 650 | 7 | |a 132971-62-1 |2 NLM | |
| 650 | 7 | |a stannane |2 NLM | |
| 650 | 7 | |a 2406-52-2 |2 NLM | |
| 700 | 1 | |a Siegel, Konrad |e verfasserin |4 aut | |
| 700 | 1 | |a Brückner, Reinhard |e verfasserin |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t Chemistry (Weinheim an der Bergstrasse, Germany) |d 1996 |g 11(2005), 5 vom: 18. Feb., Seite 1610-24 |w (DE-627)NLM09455398X |x 1521-3765 |7 nnns |
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