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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


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.

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.

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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
Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:German
Date:1996
Deposited On:25 Nov 2013 08:05
Last Modified:05 Apr 2016 17:11
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Swiss National Science Foundation, Alfred-Werner Legat, F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.1002/hlca.19960790713
Permanent URL: https://doi.org/10.5167/uzh-85397

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