Total synthesis of (–)-pateamine A, a novel immunosuppressive agent from Mycale sp

A convergent synthesis of the unique thiazole-containing polyene bis-lactone pateamine A ( 1 ) isolated from the marine sponge Mycale sp is described. The synthesis features the ubiquitous Stille sp 2 –sp 2 coupling reaction to elaborate the E,Z-diene macrolide core 23 and the all-E polyenamine side chain in the natural product. It also highlights the scope for enantiopure sulfinimine intermediates in the synthesis of chiral β-amino ester moieties in complex structures.Key words: pateamine A, immunosuppressive agent from marine sponge Mycale sp, total synthesis, novel 19-membered bis-lactone, thiazole metabolite, polyenamine, Stille reaction, sulfinimines, chiral β-amino esters.