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Optisch aktive 3-Amino-2H-azirine als Bausteine für enantiomerenreine αα-disubstituierte α-Aminosäuren: Synthese von Isovalin-Synthonen und Einbau in ein Trichotoxin-A-50-Segment

✍ Scribed by Christoph B. Bucher; Heinz Heimgartner

Publisher
John Wiley and Sons
Year
1996
Tongue
German
Weight
900 KB
Volume
79
Category
Article
ISSN
0018-019X

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✦ Synopsis

Optically Active 3‐Amino‐2__H__‐azirines as Synthons for Enantiomerically Pure αα‐Disubstiuted α‐Amino Acids: Syntheses of Isovaline Synthons and a Segment of Trichotoxin A‐50

The synthesis of a novel 3‐amino‐2‐methyl‐2‐[2‐(phenylsulfonyl)ethyl]‐2__H__‐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‐Gln‐Valol of the peptaibole Trichotoxin A‐50 and its epimer.

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Optisch aktive 3-Amino-2H-azirine als Ba
Optisch aktive 3-Amino-2H-azirine als Bausteine für enantiomerenreine α,α-disubstituierte α-Aminosäuren: Synthese des α-Methylphenylalanin-Synthons and Einbau in Modell-Peptide
✍ Christoph B. Bucher; Anthony Linden; Heinz Heimgartner 📂 Article 📅 1995 🏛 John Wiley and Sons 🌐 German ⚖ 693 KB

Optically Active 3-Amino-ZH-azirines as Synthons for Enantiomerically Pure a,a-Disubstituted a-Amino Acids: Synthesis of the a-Methylphenylalanine Synthons and Some Model Peptides The synthesis of a novel 2-benzyl-2-methyl-3-amino-ZH-azirine derivative with a chiral amino group is described. Chrom