Synthesis of the Oviposition‐Deterring Pheromone (ODP) in Rhagoletis cerasi L. Preliminary communication

For the assignment of the configuration at C(8) and C(15) of the natural oviposition‐deterring pheromone 1 in Rhagoletis cerasi L., the four possible stereoisomers of 1 are synthesized. By condensing the C 6 building blocks (5 R )‐ 4 and (5 S )‐ 4 with the boron enolates of the C 10 building blocks (4 S )‐ 13 and (4 R )‐ 13 , followed by decarboxylative dehydration, all stereoisomers of 16 are available ( Scheme 5 ). Glucosylation of 16 followed by formation of the taurin amide gives, after deprotection, the four stereoisomers (8 R ,15 S )‐ 1 , (8 R ,15 R )‐ 1 , (8 R ,15 S ) ‐1 , and (8 S ,15 S )‐ 1 ( Scheme 6 ).