Synthesis of the peptide moiety of the jamaicamides

The jamaicamides, isolated from cyanobacterium Lyngbya majuscula in Jamaica, are unique mixed polyketide-peptides that are reported to be blockers of the sodium channels. The peptide moiety contains a pyrrolinone ring and a β-methoxy enone functionality. Herein, we report the stereoselective synthesis of the N-(Boc)2-protected peptide moiety of the jamaicamides by utilizing Meldrum’s acid starting from l-alanine and N-Boc-β-alanine.