Metabolically blocked analogs of housefly sex pheromone: I. Synthesis of alternative substrates for the cuticular monooxygenases.

Cuticular monooxygenases in the cuticle of the female houseflyMusca domestica oxidize (Z)-9-tricosene to m-9,10-epoxytricosane and to (Z)-9-tricosen-14-one. One possible explanation for these two products is that a single monooxygenase accepts the alkene substrate in two different orientations. Eleven analogs of (Z)-9-tricosene bearing methyl substituents, cyclopropyl groups, fluorine substituents, deuterium substituents, and additional double bonds were synthesized to probe the substrate requirements of this monooxygenase system. In addition, the 11 corresponding epoxides were prepared to aid in identification of the metabolites of each modified alkene.