Ein neues 3-Amino-2H-azirin als Aib-Pro-Baustein: Synthese des C-terminalen Nonapeptids von Trichovirin I 1B

A New 3-Amino-2H-azirine as an Aib-Pro Synthon: Synthesis of the C-Terminal Nonapeptide of Trichovirin I 1B The synthesis of methyl N-(2,2-dimethyl-2H-azirin-3-yl)-L -prolinate ( 3 ), a novel 3-amino-2H-azirine, is described (Scheme 2). It is shown that the reaction of COCl₂ 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-2H-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).