Mild Method for Cleavage of Dehydroalanine Units: Highly Efficient Conversion of Nocathiacin I to Nocathiacin IV

Thiazolyl peptide antibacterial nocathiacin I (1) was converted to nocathiacin IV (4) in high yield using iodomethane and hydriodic acid in THF at 45 degrees C. Several simplified dehydroalanine-containing systems undergo dehydroalanine cleavage under the same conditions, although in these cases iodomethane is not needed for efficient conversion. The mild reaction conditions are in contrast with other methods described in the literature.