Total synthesis of ()-pateamine, a novel polyene bis-macrolide with immunosuppressive activity from the sponge Mycale sp.

A concise and convergent synthesis of the polyene thiazole-containing 19-membered bis-lactone ()-pateamine 1 is described. The synthesis features both the intra- and intermolecular Stille sp2–sp2 coupling reactions to elaborate the E,Z-diene macrolide core and the side-chain all-E polyene portion of the natural product, and highlights the scope for enantiopure sulfinimine intermediates in the synthesis of chiral β-amino ester moieties in complex structures.