Enantioselective synthesis of (2 S,3′ R,7′ Z)- N-(3′-hydroxy-7′-tetradecenoyl)-homoserine lactone

A flexible synthetic route was developed for the synthesis of quorum-sensing pheromone (2 S,3′ R,7′ Z)- N-(3′-hydroxy-7′-tetradecenoyl)-homoserine lactone. A key feature of this protocol is that the two stereogenic centers have been installed by means of catalytic reactions with high enantioselectivity. A concise enantioselective total synthesis of (2 S,3′ R,7′ Z)- N-(3′-hydroxy-7′-tetradecenoyl)-homoserine lactone is described. Key feature of this protocol is a catalytic asymmetric hydrogenation and a prophenol–zinc-catalyzed diazo addition to imine reaction as genesis of chirality. Moreover, flexibility is built in the synthesis to generate enantioenriched analogs using catalytic amount of enantioenriched C 2-symmetric ligands.