Bucher, Christoph B; Heimgartner, Heinz (1996). Optisch aktive 3-Amino-2H-azirine als Bausteine für enantiomerenreine alpha,alpha-disubstituierte alpha-Aminosäuren: Synthese von Isovalin-Synthonen und Einbau in ein Trichotoxin-A-50-Segment. Helvetica Chimica Acta, 79(7):1903-1915.
Abstract
The synthesis of a novel 3-amino-2-methyl-2-[2-(phenylsulfonyl)ethyl]-2H-azirine derivative 12 with a chiral substituent at the amino group is described. Chromatographic separation of the diastereoisomer mixture gave pure diastereoisomers which, after an electrochemical cleavage of the phenylsulfonyl group, yielded the (S)- and (R)-isovalin (Iva) synthons 13a and 13b, respectively. The absolute configuration of the precursor molecule 12b was established by X-ray crystallography. The Iva synthons were successfully used in the synthesis of the C-terminal pentapeptide Z-Leu-Aib-(R)-Iva-GIn-Valol of the peptaibole Trichotoxin A-50 and its epimer.
| Other titles: | Optically Active 3-Amino-2H-azirines as Synthons for Enantiomerically Pure alpha,alpha-Disubstituted alpha-Amino Acids: Syntheses of Isovaline Synthons and a Segment of Trichotoxin A-50 |
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| Item Type: | Journal Article, refereed, original work |
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| Communities & Collections: | 07 Faculty of Science > Department of Chemistry |
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| Dewey Decimal Classification: | 540 Chemistry |
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| Scopus Subject Areas: | Physical Sciences > Catalysis
Life Sciences > Biochemistry
Life Sciences > Drug Discovery
Physical Sciences > Physical and Theoretical Chemistry
Physical Sciences > Organic Chemistry
Physical Sciences > Inorganic Chemistry |
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| Uncontrolled Keywords: | Physical and Theoretical Chemistry, Inorganic Chemistry, Organic Chemistry, Biochemistry, Drug Discovery, Catalysis |
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| Language: | German |
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| Date: | 1996 |
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| Deposited On: | 25 Nov 2013 08:05 |
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| Last Modified: | 10 Mar 2025 02:38 |
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| Publisher: | Wiley-Blackwell |
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| ISSN: | 0018-019X |
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| Funders: | Swiss National Science Foundation, Alfred-Werner Legat, F. Hoffmann-La Roche AG, Basel |
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| OA Status: | Closed |
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| Publisher DOI: | https://doi.org/10.1002/hlca.19960790713 |
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| Project Information: | - Funder: SNSF
- Grant ID:
- Project Title: Swiss National Science Foundation
- Funder:
- Grant ID:
- Project Title: Alfred-Werner Legat
- Funder:
- Grant ID:
- Project Title: F. Hoffmann-La Roche AG, Basel
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Bucher, Christoph B