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

Abstract

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 COCI, 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).