A new 3-amino-2H-azirine as an Aib-Pro synthon: Synthesis of the C-terminal nonapeptide of trichovirin I 1B

Article abstract of DOI:10.1002/hlca.19960790220

The synthesis of methyl N-(2,2-dimethyl-2H-azirin-3-yl)-L-prolinate (3), a novel 3-amino-2H-azirine, is described. 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, the C-terminal 6-14 segment of the peptaibole trichovirin I 1B. The structure of 17 was established by single-crystal X-ray crystallography.