Premium
Ein neues 3‐Amino‐2 H ‐azirin als Aib‐Pro‐Baustein: Synthese des C‐terminalen Nonapeptids von Trichovirin I 1B
Author(s) -
Luykx Roeland,
Bucher Christoph B.,
Linden Anthony,
Heimgartner Heinz
Publication year - 1996
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19960790220
Subject(s) - chemistry , azirine , dipeptide , thioamide , synthon , stereochemistry , yield (engineering) , amino acid , ring (chemistry) , organic chemistry , biochemistry , materials science , metallurgy
A New 3‐Amino‐2 H ‐azirine as an Aib‐Pro Synthon: Synthesis of the C‐Terminal Nonapeptide of Trichovirin I 1B The synthesis of methyl N ‐(2,2‐dimethyl‐2 H ‐azirin‐3‐yl)‐ L ‐prolinate ( 3 ), a novel 3‐amino‐2 H ‐azirine, is described ( Scheme 2 ). It is shown that the reaction of COCl 2 with thioamide 5 is remarkably faster than with the corresponding amide 4 , and the yield of 3 is much better in the synthesis starting with 5 . The 3‐amino‐2 H ‐azirine 3 has been used as a building block of the dipeptide moieties Aib‐Pro in the synthesis of nonapeptide 17 ( Schemes 4 and 5 ), the C‐terminal 6–14 segment of the peptaibole trichovirin I 1B. The structure of 17 was established by single‐crystal X‐ray crystallography ( Figs.1 and 2 ).