A novel semi-synthesis of spinetoram-J based on the selective hydrolysis of 5,6-dihydro spinosyn A

Spinetoram is a novel kind of fermentation-derived insecticide with a broad range of action against lots of insect pests. Due to the broad pest spectrum, high insecticidal activity, low environmental impact, and low toxicity to non-target species, spinetoram has been widely applied in pest control and stored-grain protection. Spinetoram is a mixture of spinetoram-J (XDE-175-J, major component) and spinetoram-L (XDE-175-L). In this study, a novel selective hydrolysis of C9-glycosidic bond of 5,6-dihydro spinosyn A was developed. And a 3-step semi-synthesis of spinetoram-J based on the selective hydrolysis was designed and discussed. All compounds in the synthesis were characterized by 1H NMR, 13C NMR and mass spectrum. In addition, the improved semi-synthesis also provides an efficient way to synthesize the rhamnose replacement analogues of spinetoram-J which may be promising in the pest control and fungus control.

Natural products; improved semi-synthesis; selective hydrolysis; spinetoram.